Diisopropylethylamine → 5-(6-(5,6,7,8-tetrahydro-4H-thiazolo[5,4-d]azepine-6-carbonyl)pyrimidin-4-ylamino)-1,3-di-hydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1640297Notes

Reaction equation

HRID 1640297 reaction equation
Cl.[O:2]=[C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]21[CH2:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([NH:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([C:27]([OH:29])=O)[CH:22]=3)[CH:17]=1)[CH2:12]2.[S:30]1[C:39]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34][C:33]=2[N:32]=[CH:31]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[S:30]1[C:39]2[CH2:38][CH2:37][N:36]([C:27]([C:23]3[N:24]=[CH:25][N:26]=[C:21]([NH:20][C:16]4[CH:17]=[C:18]5[C:13](=[CH:14][CH:15]=4)[CH2:12][C:4]4([C:5]6[C:6](=[N:7][CH:8]=[CH:9][CH:10]=6)[NH:11][C:3]4=[O:2])[CH2:19]5)[CH:22]=3)=[O:29])[CH2:35][CH2:34][C:33]=2[N:32]=[CH:31]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226207475,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineHCID 667221856-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl-amino)pyrimidine-4-carboxylic acid-hydrochloride

Product 1

HCID 498019805-(6-(5,6,7,8-tetrahydro-4H-thiazolo[5,4-d]azepine-6-carbonyl)pyrimidin-4-ylamino)-1,3-di-hydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

86 mg (0.21 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 37 mg (0.24 mmol) 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine, 0.13 mL (0.72 mmol) DIPEA and 77 mg (0.24 mmol) TBTU in 1.0 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised.

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-4b64c0ac052543fa97d1c39f7de965f7
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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