Ammonium Chloride → HCID 57955598, compound

HRID 914112Notes

Reaction equation

[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:35](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+]>>[CH:1]1([N:7]2[CH2:13][C:12]([F:14])([F:15])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([NH2:35])=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 25517Ammonium Chloride

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

HCID 252536804-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid

Product 1

HCID 57955598HCID 57955598, compound

Procedure

The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-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 ammonium chloride. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10-1.41 (m, 3H) 1.54-1.86 (m, 7H) 3.32 (s, 3H) 3.93 (s, 3H) 4.17 (t, J=12.5 Hz, 2H) 4.44-4.55 (m, 1H) 7.33 (s, 1H) 7.55 (d, J=8.3 Hz, 1H) 7.59 (s, 1H) 7.99 (s, 1H) 8.13 (d, J=8.1 Hz, 1H) 8.24 (s, 1H) 8.61 (s, 1H). [M+H] calc'd for C22H26F2N6O3 461. found 461.

Workup

customas described in the General procedure for amide bond synthesis
customThe final compound was purified by reverse phase HPLC
customto give the free base

Sources & evidence

ORD record: ord-fc3dfa2910b44a738a8dae8d3b18e6d7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026234B2

Reaction notes

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