Aniline → HCID 50995471, compound

HRID 1772825Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([N:18]3[CH:22]=[C:21]([C:23]4[C:24]5[CH:31]=[CH:30][NH:29][C:25]=5[N:26]=[CH:27][N:28]=4)[CH:20]=[N:19]3)[CH2:15][C:16]#[N:17])[CH2:10][CH2:9]2)[C:3]=1[CH3:32].[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[NH:33]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([N:18]3[CH:22]=[C:21]([C:23]4[C:24]5[CH:31]=[CH:30][NH:29][C:25]=5[N:26]=[CH:27][N:28]=4)[CH:20]=[N:19]3)[CH2:15][C:16]#[N:17])[CH2:10][CH2:9]2)[C:3]=1[CH3:32])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 6115Aniline

HCID 58180905HCID 58180905, compound

Product 1

HCID 50995471HCID 50995471, compoundYield 35.2%

Procedure

A solution of 3-[1-(6-chloro-5-methylpyrimidin-4-yl)piperidin-4-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.0081 g, 0.018 mmol) in Aniline (95 uL, 1.0 mmol) was heated at 180° C. for 2.5 hours. The reaction was purified by preparative-LCMS (pH 10) to give 3.2 mg white solid (35% yield). 1H NMR (400 MHz, DMSO): δ 12.05 (1H, br); 8.77 (1H, s); 8.61 (1H, s); 8.58 (1H, s); 8.15 (1H, s); 8.1 (1H, s); 7.55 (1H, d); 7.53 (2H, m); 7.2 (2H, t); 6.92 (1H, d); 6.9 (1H, m); 4.57 (1H, m); 3.6 (1H, m); 3.45 (1H, m); 3.27 (2H, m); 2.7 (1H, m); 2.58 (1H, m); 2.02 (1H, m); 1.98 (3H, s); 1.85 (1H, m); 1.3 (2H, m); 1.01 (1H, m). LCMS (M+1): 505.

Workup

customThe reaction was purified by preparative-LCMS (pH 10)

Sources & evidence

ORD record: ord-0b65ef8076334ea69e8ff3e879acfca8
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249145B2

Reaction notes

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