Diisopropylethylamine → 3-(1-(6-((4aR,8aS)-decahydroisoquinoline-2-carbonyl)pyrimidin-4-yl)piperidin-4-yl)-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

HRID 74675Notes

Reaction equation

HRID 74675 reaction equation
CO[C:3]1[CH:14]=[CH:13][C:6]2N[C:8](=O)[NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[NH:26][C:25](=[O:27])[N:24]([CH:28]3[CH2:33][CH2:32][N:31]([C:34]4[N:39]=[CH:38][N:37]=[C:36]([C:40](O)=[O:41])[CH:35]=4)[CH2:30][CH2:29]3)[CH2:23][CH2:22][C:21]=2[CH:43]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:8]1[C@@H:6]2[C@H:5]([CH2:4][CH2:3][CH2:14][CH2:13]2)[CH2:11][CH2:10][N:9]1[C:40]([C:36]1[N:37]=[CH:38][N:39]=[C:34]([N:31]2[CH2:32][CH2:33][CH:28]([N:24]3[CH2:23][CH2:22][C:21]4[CH:43]=[C:17]([O:16][CH3:15])[CH:18]=[CH:19][C:20]=4[NH:26][C:25]3=[O:27])[CH2:29][CH2:30]2)[CH:35]=1)=[O:41]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583866166-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acidHCID 866565007-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Product 1

HCID 673381573-(1-(6-((4aR,8aS)-decahydroisoquinoline-2-carbonyl)pyrimidin-4-yl)piperidin-4-yl)-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Analogously to decahydroisoquinoline-2-carbonyl)pyrimidin-4-yl)piperidin-4-yl)-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one the following compounds were prepared from 4.0 mg (10 μmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 3.6 mg (11 μmol) TBTU, 12 μmol of the corresponding amine and 3.9 μL DIPEA in 350 μL DMF:

Sources & evidence

ORD record
ord-0179ff19cc2b4e7cb2cc97cd4ea89984
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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