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4-Methylmorpholine → 2-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-[6-[5-[(ethenylsulfonyl)amino]-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 1695743
Notes
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Reaction equation

HRID 1695743 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([NH:25][C:26]([C:28]3[N:29]=[C:30]([CH2:33][N:34]4[CH2:39][C@H:38]([CH3:40])[O:37][C@H:36]([CH3:41])[CH2:35]4)[S:31][CH:32]=3)=[O:27])[C:13]3[C:17]([CH:18]=2)=[N:16][N:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:14]=3)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].CN1CCOCC1.Cl[CH2:50][CH2:51][S:52](Cl)(=[O:54])=[O:53]>C(Cl)Cl>[CH3:41][C@H:36]1[O:37][C@@H:38]([CH3:40])[CH2:39][N:34]([CH2:33][C:30]2[S:31][CH:32]=[C:28]([C:26]([NH:25][C:12]3[C:13]4[C:17]([CH:18]=[C:10]([C:4]5[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][S:52]([CH:51]=[CH2:50])(=[O:54])=[O:53])[CH:3]=5)[CH:11]=3)=[N:16][N:15]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[CH:14]=4)=[O:27])[N:29]=2)[CH2:35]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 58255790N-[6-[5-Amino-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide

Product 1

HCID 669112332-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-[6-[5-[(ethenylsulfonyl)amino]-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-[6-[5-Amino-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide (250 mg) was dissolved in DCM (6 ml) and N-methylmorpholine (0.143 ml) was added. The reaction was cooled to 0° C. in an ice bath, then 2-chloroethanesulfonyl chloride (0.047 ml) was added dropwise. The reaction was left to warm to RT overnight. Reaction had blown dry, so was redissolved in DCM (6 ml). Further 2-chloroethanesulfonyl chloride (0.047 ml) was added and stirred at RT for 2 hours. Water (6 ml) was added to the reaction. The DCM was separated, passed through a hydrophobic frit, then evaporated to dryness to give crude title compound (250 mg) used directly in the next step without further purification.

Workup

  1. waitThe reaction was left
  2. temperatureto warm to RT overnight
  3. customReaction
  4. customhad blown dry
  5. dissolutionso was redissolved in DCM (6 ml)
  6. additionFurther 2-chloroethanesulfonyl chloride (0.047 ml) was added
  7. additionWater (6 ml) was added to the reaction
  8. customThe DCM was separated
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-3f2ecda3e6c54712b7e253593f95a53e
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes