HCID 67818204, compound → HCID 67819081, compound

HRID 2279812Notes

Reaction equation

HRID 2279812 reaction equation
NC1C(C(NC)=O)=NC(C2C(C)=NN(CCCO)C=2)=CC=1.[NH2:22][C:23]1[C:24]([C:46]([NH:48][CH3:49])=[O:47])=[N:25][C:26]([C:29]2[CH:30]=[N:31][N:32]([CH2:35][CH2:36][CH2:37][O:38]CC3C=CC=CC=3)[C:33]=2[CH3:34])=[CH:27][CH:28]=1>>[NH2:22][C:23]1[C:24]([C:46]([NH:48][CH3:49])=[O:47])=[N:25][C:26]([C:29]2[CH:30]=[N:31][N:32]([CH2:35][CH2:36][CH2:37][OH:38])[C:33]=2[CH3:34])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 67818204HCID 67818204, compound2×HCID 866977493-Amino-6-[1-(3-hydroxypropyl)-3-methyl-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

Product 1

HCID 67819081HCID 67819081, compoundYield 54.1%

Procedure

Prepared analogously to Compound 34C replacing Compound 34D with 3-amino-6-{1-[3-(benzyloxy)propyl]-5-methyl-1H-pyrazol-4-yl}-N-methylpyridine-2-carboxamide (Compound 34E, 429 mg, 1.13 mmol) to afford 177 mg of the title compound (54%). 1H NMR (400 MHz, CD3OD) δ 7.75 (s, 1H), 7.35 (d, J=8.8 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 4.18 (t, J=7.1 Hz, 2H), 3.51 (t, J=6.2 Hz, 2H), 2.89 (s, 3H), 2.51 (s, 3H), 1.97 (quin, J=6.6 Hz, 2H). MS (ESI): m/z=290.57 [M+H]+. UPLC: tR=0.67 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-f358f2e3fdb04df8b1c9996a7b891cf3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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