tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 57955536, compound

HRID 1880950Notes

Reaction equation

HRID 1880950 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=[N:50][C:45]2[CH:46]=[CH:47][CH:48]=[N:49][C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N1CCC[C@@H](N)C1)(OC(C)(C)C)=O>>[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:50][C@@H:45]5[CH2:46][CH2:47][CH2:48][NH:49][CH2:44]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 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 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 57955536HCID 57955536, compound

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 (R)-1-Boc-3-aminopiperidine. Further, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group was removed using 40% TFA in dichloromethane (6 ml) and purified the product using preparative HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41-2.00 (m, 12 H) 2.39 (t, J=6.5 Hz, 2 H) 2.81 (d, J=12.38 Hz, 1 H) 2.96 (d, J=12.38 Hz, 1 H) 3.28 (s, 3 H) 3.70-3.88 (m, 3 H) 3.94 (s, 2 H) 4.88 (m, 1 H) 5.37 (d, 2 H) 6.00 (m, 1 H) 7.47 (d, J=8.0 Hz, 1 H), 7.48 (br. s., 1 H) 7.82 (s, 1 H) 7.98 (d, J=8.0 Hz, 1 H) 8.12 (s, 1 H) 8.30 (d, J=8.0 Hz, 1 H). Melting point: 169-172° C. [M+H] calculated for C28H36FN7O3, 538; found 538.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. washFurther, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group
  3. customwas removed
  4. custompurified the product

Sources & evidence

ORD record
ord-2221c8bca8ef4941b21cc0ed60314406
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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