(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate → (S)-5-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxamide

HRID 2088442Notes

Reaction equation

HRID 2088442 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14]C(=O)OC(C)(C)C)[CH2:9]1.C(OC([NH:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][N:36]=2)=[N:32][C:31]=1[C:42](O)=[O:43])=O)(C)(C)C>>[NH2:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][N:36]=2)=[N:32][C:31]=1[C:42]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH2:14])[CH2:9]1)=[O:43]

Participants

3

Reactant 2

HCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamateHCID 698113535-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid

Product 1

HCID 58182158(S)-5-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxamideYield 55%

Procedure

Followed the procedure as described in EXAMPLE 1, starting with (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate and 5-(tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid. Obtained the desired product as a white solid (50 mg, 55%). 1H NMR (500 MHz, DMSO) δ 9.40 (s, 1H), 8.44 (d, J=4.6 Hz, 1H), 8.21 (d, J=5.2 Hz, 1H), 7.86 (dd, J=25.8, 14.5 Hz, 3H), 7.58-7.40 (m, 1H), 7.13 (d, J=5.2 Hz, 1H), 3.09 (d, J=9.1 Hz, 1H), 3.00 (d, J=12.6 Hz, 2H), 2.59 (dd, J=26.2, 15.4 Hz, 1H), 2.37 (t, J=10.1 Hz, 1H), 1.90 (s, 1H), 1.78 (d, J=15.8 Hz, 2H), 1.14 (d, J=8.7 Hz, 1H). ESIMS m/z=414.1 (M+1).

Sources & evidence

ORD record
ord-14a960e3449046f3a719f8c63ed655e2
Source dataset
uspto-grants-2013_05
Patent number
US08435976B2

Reaction notes

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