Isopropyl chloroformate → HCID 67344420, compound

HRID 451489Notes

Reaction equation

HRID 451489 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.Cl[C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:25]2[CH2:26][CH2:27][N:28]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:29][CH:30]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 67343110HCID 67343110, compound

Product 1

HCID 67344420HCID 67344420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in analogy to example 164b, starting from 6-methyl-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-8-(1,2,3,6-tetrahydropyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine and isopropyl chloroformate. The title compound was obtained as a colorless solid (yield: 32%) after column chromatography on silica gel using a gradient from methylene chloride to a mixture of methylene chloride/methanol 19:1 (v/v) as eluent. MS ISP (m/e): 491.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): (ppm)=8.51 (s, 1H), 8.04 (s, 1H), 7.16 (br s, 1H), 7.11 (s, 1H), 6.41 (s, 1H), 4.97 (sept, 1H), 4.39 (d, 1H), 4.31 (br d, 2H), 4.21 (br s, 2H), 3.96 (m, 1H), 3.72 (t, 1H), 3.18 (t, 2H), 2.63 (br s, 2H), 2.37 (s, 3H), 2.34 (s, 3H), 2.21 (br d, 2H), 1.53 (m, 2H), 1.26 (d, 6H).

Workup

  1. customPrepared in analogy to example 164b

Sources & evidence

ORD record
ord-1b0027c622ec4a88af564cab4e735a58
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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