4-Amino-1-methylpiperidine → 4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

HRID 1880947Notes

Reaction equation

HRID 1880947 reaction equation
[CH:1]1([N:7]2[CH2:13][C:12]([F:16])([CH:14]=[CH2:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]3[CH:19]=[N:20][C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:8]2=3)C[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:59][CH:60]1[CH2:65][CH2:64][N:63]([CH3:66])[CH2:62][CH2:61]1>>[CH:1]1([N:7]2[CH2:13][C:12]([F:16])([CH:14]=[CH2:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]3[CH:19]=[N:20][C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([NH:59][CH:60]5[CH2:65][CH2:64][N:63]([CH3:66])[CH2:62][CH2:61]5)=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:8]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67117825HCID 67117825, compound

Product 1

HCID 252530694-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

Procedure

The title compound was synthesized from 4-(9-cyclohexyl-7-fluoro-7-vinyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and 4-amino 1-N-methyl piperidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53-1.86 (m, 8 H) 1.93 (t, J=10.86 Hz, 4 H) 2.16 (s, 3 H) 2.78 (d, J=11.12 Hz, 2 H) 3.28 (s, 3 H) 3.65-3.83 (m, 4 H) 3.93 (s, 3 H) 4.88 (m, 1 H) 5.38 (d, J=11.87 Hz, 2 H) 6.01 (m, 1 H) 7.48 (d, J=8.0 Hz, 1 H), 7.49 (br. s., 1 H) 7.82 (s, 1 H) 8.12 (s, 1 H) 8.12 (d, J=7.83 Hz, 1 H) 8.30 (d, J=8.0 Hz, 1 H). [M+H] calculated for C29H38FN7O3, 552; found 552.

Workup

  1. customas described in the General procedure for amide bond synthesis

Sources & evidence

ORD record
ord-bf6b97eddf29476dbde0a1880a3e5153
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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