Isopropyl chloroformate → HCID 59856706, compound

HRID 1174805Notes

Reaction equation

HRID 1174805 reaction equation
[CH:1]1([N:4]([C:12]2[C:17]([CH3:18])=[C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=3[F:30])[N:15]=[CH:14][N:13]=2)[CH2:5][CH:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40]>C1COCC1>[CH:42]([O:41][C:39]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][N:4]([CH:1]2[CH2:3][CH2:2]2)[C:12]2[C:17]([CH3:18])=[C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][C:21]=3[F:30])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:8]1)=[O:40])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 67203036HCID 67203036, compound

Product 1

HCID 59856706HCID 59856706, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cyclopropyl-[6-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-pyrimidin-4-yl]-piperidin-4-ylmethyl-amine (65 mg, 0.15 mmole) and triethylamine (23 mg, 0.225 mmole) in 2 mL THF was stirred at room temperature for 10 minutes. Into this mixture was added drop-wise isopropyl chloroformate (0.225 mmole). The mixture was quenched with water, extracted with ethyl acetate, and dried in vacuum to give Compound D2 as a yellow solid (65 mg, 83%). 1H NMR (CDCl3, 400 MHz) δ 0.69-0.64 (m, 2H), 0.83-0.88 (m, 2H), 1.12-1.15 (m, 2H), 1.23 (d, J=6.3 Hz, 6H), 1.72 (d, J=13.1 Hz, 2H), 1.94-2.02 (m, 1H), 2.04 (s, 3H), 2.73 (t, J=12.4 Hz, 2H), 2.97-3.17 (m, 1H), 3.10 (s, 3H), 3.49-3.55 (m, 2H), 4.09-4.23 (m, 2H), 4.90 (sept, J=6.3 Hz, 1H), 7.45 (t, J=8.3 Hz, 1H), 7.76-7.80 (m, 2H), 8.12 (s, 1H). Exact mass calculated for C25H33FN4O5S 520.2, found 521.5 (MH+).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customdried in vacuum

Sources & evidence

ORD record
ord-edc74b97619d48bfb063487769e91508
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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