1-(Trifluoromethyl)cyclopropanamine → HCID 71143631, compound

HRID 2363307Notes

Reaction equation

HRID 2363307 reaction equation
[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]3[C:23]4[CH:30]=[CH:29][N:28](COCC[Si](C)(C)C)[C:24]=4[N:25]=[CH:26][N:27]=3)[CH:19]=[N:18]2)[CH2:7][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14](O)=[O:15])=[N:12][CH:13]=2)[CH2:5]1)#[N:2].[F:39][C:40]([F:46])([F:45])[C:41]1([NH2:44])[CH2:43][CH2:42]1>>[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]3[C:23]4[CH:30]=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH:19]=[N:18]2)[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:44][C:41]3([C:40]([F:46])([F:45])[F:39])[CH2:43][CH2:42]3)=[O:15])=[N:12][CH:13]=2)[CH2:7]1)#[N:2]

Participants

3

Reactant 2

HCID 116511971-(Trifluoromethyl)cyclopropanamineHCID 711436565-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyridine-2-carboxylic acid

Product 1

HCID 71143631HCID 71143631, compound

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 12, Step 3 starting from 5-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyridine-2-carboxylic acid (Example 12, Step 2) and 1-(trifluoromethyl)cyclopropanamine (Oakwood Products, Inc., Cat. #: 038175). LCMS (M+H)+: m/z=508.2. 1H NMR (400 MHz, DMSO-d6): δ 12.69 (br, 1H), 9.12 (s, 1H), 9.11 (d, J=2.9 Hz, 1H), 8.87 (s, 1H), 8.59 (s, 1H), 7.95 (d, =2.7 Hz, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.84-7.80 (br, 1H), 7.26 (dd, J=2.1, 1.3 Hz, 1H), 7.11 (dd, J=8.7, 2.8 Hz, 1H), 4.70 (d, J=9.1 Hz, 2H), 4.44 (d, J=9.2 Hz, 2H), 3.80 (s, 2H), 1.28 (m, 2H), 1.17 (m, 2H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-6c58f0f90ab04da8a5eaaeff4f6c9175
Source dataset
uspto-grants-2014_04
Patent number
US08691807B2

Reaction notes

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