Ammonia → HCID 67391837, compound

HRID 406100Notes

Reaction equation

HRID 406100 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[NH:22][C:23]2[C:24]3[C:31]([CH3:32])=[C:30]([C:33]([OH:35])=O)[S:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:37](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N>C1COCC1.O1CCOCC1.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[NH:22][C:23]2[C:24]3[C:31]([CH3:32])=[C:30]([C:33](=[O:35])[NH2:37])[S:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58421631HCID 58421631, compound

Product 1

HCID 67391837HCID 67391837, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-[2-((1S,3S)-3-tert-butoxycarbonylamino-cyclopentyloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (115 mg), TBTU (81 mg) and DIPEA (88 μl) in THF (15 ml) was stirred at rt for 30 minutes. After the addition of 0.5 M ammonia in dioxane (458 μl) and DMF the mixture was stirred at rt overnight. The reaction mixture was concentrated, diluted with water and extracted with DCM. The organic layer was concentrated and the crude was purified by chromatography to give the desired product.

Workup

  1. stirringwas stirred at rt overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with DCM
  5. concentrationThe organic layer was concentrated
  6. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-bdc985b59acb4f3187143e300736f8c7
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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