2-Morpholinoethylamine → HCID 46237017, compound

HRID 28954Notes

Reaction equation

HRID 28954 reaction equation
[CH:1]([C:3]1[N:34]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[C:6]2=[N:7][CH:8]=[CH:9][C:10]([C:11]3[C:12]([C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:26])=[CH:20][CH:19]=4)=[N:13][N:14]([CH2:16][CH3:17])[CH:15]=3)=[C:5]2[CH:4]=1)=O.[NH2:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH2:16]([N:14]1[CH:15]=[C:11]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]3[N:34]([S:35]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)(=[O:36])=[O:37])[C:3]([CH2:1][NH:44][CH2:45][CH2:46][N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[CH:4][C:5]=23)[C:12]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])=[CH:20][CH:19]=2)=[N:13]1)[CH3:17]

Participants

6

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 46236618N-(4-{4-[2-formyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-ethyl-1H-pyrazol-3-yl}phenyl)-N'-phenylurea

Product 1

HCID 46237017HCID 46237017, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-{4-[2-formyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-ethyl-1H-pyrazol-3-yl}phenyl)-N′-phenylurea (0.1 mmol), 4-(2-aminoethyl)-morpholine (0.2 mmol), and sodium triacetoxyborohydride (0.2 mmol) in dichloromethane (1 mL) and acetic acid (0.25 mL) under nitrogen was stirred at room temperature for 30 minutes. The reaction was quenched with 1N sodium hydroxide solution (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, and concentrated in vacuo to give the title compound as the crude product. ESMS [M+H]+: 705.6

Workup

  1. customThe reaction was quenched with 1N sodium hydroxide solution (5 mL)
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined organic layers were washed with brine (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1223d13a4fba4f23895cba4d9c90829a
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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