1-(Cyclopropylmethyl)piperazine → HCID 57955538, compound

HRID 1880983Notes

Reaction equation

HRID 1880983 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26]([OH:28])=O)=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[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.[CH:58]1([CH2:61][N:62]2[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]2)[CH2:60][CH2:59]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:23]=[C:24]([F:33])[C:25]([C:26]([N:65]5[CH2:66][CH2:67][N:62]([CH2:61][CH:58]6[CH2:60][CH2:59]6)[CH2:63][CH2:64]5)=[O:28])=[CH:29][C:30]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 9658751-(Cyclopropylmethyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252536794-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid

Product 1

HCID 57955538HCID 57955538, compound

Procedure

The title compound was synthesized from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid as described in the general procedure for amide bond synthesis using HATU and 1-(cyclopropylmethyl)piperazine. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.07 (d, J=4.55 Hz, 2 H) 0.45 (d, J=8.08 Hz, 2 H) 0.75-0.87 (m, 1 H) 1.47-1.77 (m, 6 H) 1.92 (br. s., 2 H) 2.20 (d, J=6.57 Hz, 2 H) 2.32-2.43 (m, 2 H) 3.22-3.31 (m, 2 H) 3.64 (br. s., 2 H) 3.88 (s, 3 H) 4.06 (t, J=13.77 Hz, 3 H) 4.70-4.84 (m, 1 H) 6.97 (d, J=6.06 Hz, 1 H) 8.04 (s, 1 H) 8.16 (d, J=11.87 Hz, 1 H) 8.28 (s, 1 H). [M+H] calculated for C29H36F3N7O3, 588; found 588.

Workup

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

Sources & evidence

ORD record
ord-f3a5a1a12a2849e88cd9e35567a90319
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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