HCID 67437230, compound → HCID 58465054, compound

HRID 2089416Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[NH2:15])[CH2:5][CH2:4]1.C(OC([NH:23][C:24]1[S:28][C:27]([CH:29]2[CH2:32][CH2:31][CH2:30]2)=[N:26][C:25]=1[C:33](O)=[O:34])=O)(C)(C)C>>[NH2:23][C:24]1[S:28][C:27]([CH:29]2[CH2:32][CH2:31][CH2:30]2)=[N:26][C:25]=1[C:33]([NH:15][C:10]1[CH:11]=[N:12][N:13]([CH3:14])[C:9]=1[N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4][CH2:5]1)=[O:34]

Participants

Reactant 2

HCID 67437230HCID 67437230, compound

HCID 67439191HCID 67439191, compound

Product 1

HCID 58465054HCID 58465054, compoundYield 37%

Procedure

Following the procedure for Example 304 starting with 5-(4-(aminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-amine and 5-(tert-butoxycarbonylamino)-2-cyclobutylthiazole-4-carboxylic acid gave 305 as a white solid (44 mg, 37% over two steps). 1H NMR (400 MHz, d4-MeOD) δ 7.45 (s, 1H), 3.75-3.62 (m, 4H), 3.23-3.07 (m, 4H), 2.60 (d, J=6.5 Hz, 2H), 2.47-2.29 (m, 4H), 2.17-2.01 (m, 1H), 2.00-1.90 (m, 1H), 1.84 (d, J=12.5 Hz, 2H), 1.56-1.43 (m, 1H), 1.36 (qd, J=11.9, 4.4 Hz, 2H). LCMS (ES+) m/z 390 (M+1)

Sources & evidence

ORD record: ord-682f188fe7e84d799f2a7dc4d4f6d7bb
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436001B2

Reaction notes

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