(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate → HCID 51002194, compound

HRID 2088434Notes

Reaction equation

HRID 2088434 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])=[N:11][C:10]=1[C:22]([OH:24])=O)=O)(C)(C)C.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([NH:38]C(=O)OC(C)(C)C)[CH2:33]1>>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[N:11][C:10]=1[C:22]([NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([NH2:38])[CH2:33]1)=[O:24]

Participants

3

Reactant 2

HCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamateHCID 69811461HCID 69811461, compound

Product 1

HCID 51002194HCID 51002194, compoundYield 13%

Procedure

Followed the procedure as described in EXAMPLE 1, starting with 5-(tert-butoxycarbonylamino)-2-(2,6-dimethylphenyl)thiazole-4-carboxylic acid and (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate. Obtained the desired product as a white solid (8 mg, 13%). 1H NMR (400 MHz, DMSO) δ 9.22 (s, 1H), 8.18 (d, J=5.3 Hz, 1H), 7.48 (s, 2H), 7.35-7.26 (m, 1H), 7.17 (d, J=7.7 Hz, 2H), 7.04 (d, J=5.3 Hz, 1H), 3.06 (t, J=14.4 Hz, 1H), 2.99 (d, J=11.7 Hz, 1H), 2.83-2.66 (m, 1H), 2.64-2.48 (m, 1H), 2.45-2.31 (m, 1H), 2.21 (s, 6H), 1.64 (dd, J=17.0, 6.8 Hz, 2H), 1.57-1.41 (m, 1H), 1.17-0.95 (m, 1H). ESIMS m/z=423.2 (M+1).

Sources & evidence

ORD record
ord-34f959b43868432282cfa998ad975827
Source dataset
uspto-grants-2013_05
Patent number
US08435976B2

Reaction notes

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