(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate → HCID 51002102, compound

HRID 2088433Notes

Reaction equation

C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[CH:19]=[C:18]([C:20](=[O:25])[NH:21][CH:22]([CH3:24])[CH3:23])[CH:17]=[CH:16][C:15]=2[F:26])=[N:11][C:10]=1[C:27]([OH:29])=O)=O)(C)(C)C.[NH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][CH2:40][C@H:39]([NH:43]C(=O)OC(C)(C)C)[CH2:38]1>>[NH2:8][C:9]1[S:13][C:12]([C:14]2[CH:19]=[C:18]([C:20](=[O:25])[NH:21][CH:22]([CH3:23])[CH3:24])[CH:17]=[CH:16][C:15]=2[F:26])=[N:11][C:10]=1[C:27]([NH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][CH2:40][C@@H:39]([NH2:43])[CH2:38]1)=[O:29]

Participants

Reactant 2

HCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate

HCID 69810293HCID 69810293, compound

Product 1

HCID 51002102HCID 51002102, compoundYield 8%

Procedure

Followed the procedure as described in EXAMPLE 1, starting with 5-(tert-butoxycarbonylamino)-2-(2-fluoro-5-(isopropylcarbamoyl)phenyl)thiazole-4-carboxylic acid and (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate. Obtained the desired product as a white solid (5 mg, 8%). 1H NMR (400 MHz, DMSO) δ 9.37 (s, 1H), 8.61 (dd, J=7.4, 2.2 Hz, 1H), 8.46 (d, J=7.6 Hz, 1H), 8.30 (s, 1H), 8.23 (d, J=5.3 Hz, 1H), 7.98-7.86 (m, 1H), 7.69 (s, 2H), 7.48 (dd, J=11.3, 8.7 Hz, 1H), 7.14 (d, J=5.3 Hz, 1H), 4.13 (td, J=13.5, 6.8 Hz, 1H), 3.20 (d, J=8.8 Hz, 9H), 3.01 (d, J=12.1 Hz, 2H), 2.70 (d, J=18.9 Hz, 1H), 1.89 (d, J=9.6 Hz, 1H), 1.78 (d, J=22.6 Hz, 2H), 1.40-1.23 (m, 1H), 1.19 (d, J=6.6 Hz, 6H). ESIMS m/z=498.2 (M+1).

Sources & evidence

ORD record: ord-af93419f4b114726b9648740e0cf3e6c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435976B2

Reaction notes

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