(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate → HCID 51002152, compound

HRID 2088437Notes

Reaction equation

C(OC([NH:8][C:9]1[S:13][C:12]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:11][C:10]=1[C:19]([OH:21])=O)=O)(C)(C)C.[NH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[N:29]1[CH2:34][CH2:33][CH2:32][C@H:31]([NH:35]C(=O)OC(C)(C)C)[CH2:30]1>>[NH2:8][C:9]1[S:13][C:12]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[N:11][C:10]=1[C:19]([NH:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[N:29]1[CH2:34][CH2:33][CH2:32][C@H:31]([NH2:35])[CH2:30]1)=[O:21]

Participants

Reactant 2

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

HCID 69809381HCID 69809381, compound

Product 1

HCID 51002152HCID 51002152, compoundYield 48%

Procedure

Followed the procedure as described in EXAMPLE 1, starting with 5-(tert-butoxycarbonylamino)-2-cyclopentylthiazole-4-carboxylic acid and (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate. Obtained the desired product as a white solid (22 mg, 48%). 1H NMR (500 MHz, DMSO) δ 9.39 (s, 1H), 8.18 (d, J=5.2 Hz, 1H), 7.24 (s, 1H), 7.10 (d, J=5.3 Hz, 1H), 3.23 (m, 3H), 3.07 (d, J=10.5 Hz, 1H), 2.96 (d, J=9.7 Hz, 2H), 2.67-2.53 (m, 2H), 2.43-2.34 (m, 1H), 2.03 (d, J=8.1 Hz, 2H), 1.87 (d, J=12.5 Hz, 1H), 1.84-1.58 (m, 5H), 1.17 (d, J=13.3 Hz, 1H). ESIMS m/z=387.2 (M+1).

Sources & evidence

ORD record: ord-ad177e3cf1764a27b6dab6ffee7e867e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435976B2

Reaction notes

Loading…