Isopropyl chloroformate → HCID 24994031, compound

HRID 423503Notes

Reaction equation

HRID 423503 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C.Cl[C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38]>ClCCl>[F:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][CH:22]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 66672772HCID 66672772, compound

Product 1

HCID 24994031HCID 24994031, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (83 mg, 92%) was prepared as a white solid from 4-({[3-fluoro-4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride (80 mg, 0.20 mmol), diisopropylethylamine (0.11 mL, 0.60 mmol), isopropyl chloroformate (1.0M in toluene, 0.22 mL, 0.22 mmol) and dichloromethane (6 mL) in a manner similar to Example 66, Step 2. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, 2H, J=8.3 Hz), 7.70 (d, 2H, J=8.3 Hz), 7.40-7.25 (m, 2H), 7.10-7.00 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.22 (bs, 2H), 3.92 (d, 2H, J=6.4 Hz), 3.08 (s, 3H), 2.85-2.70 (m, 2H), 2.15-2.00 (m, 1H), 1.95-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 450 (M+H).

Sources & evidence

ORD record
ord-ec7927b874ba4c13a92aee2ae5050ad3
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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