Trifluoroacetic acid → HCID 57955563, compound
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](O)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:34][C@@H:35]1[CH2:40][CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36]1.C(O)(C(F)(F)F)=O>>[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]([NH:34][C@@H:35]5[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]5)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
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 and (R)-tert-butyl 3-aminopiperidine-1-carboxylate as described in the General procedure for amide bond synthesis. The Boc group was then deprotected using TFA. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (m, 3 H) 1.61 (m, 9 H) 1.99 (s, 3 H) 2.73 (m, 1 H) 2.93 (m, 1 H) 3.92 (s, 4 H) 4.01-4.20 (t, J=14 Hz, 2 H) 4.82 (m, 1 H) 7.24 (d, J=6.8 Hz, 1 H) 7.71-7.90 (m, 1 H) 8.05 (s, 1 H) 8.14-8.38 (m, 2 H). [M+H] calc'd for C26H32F3N7O3, 548; found 548.
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-90466a9787bc4619a0df205b31e0a480
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318727B2
Reaction notes
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