Methyl chloroformate → HCID 44242164, compound

HRID 627848Notes

Reaction equation

HRID 627848 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[N:12][N:11]=[C:10]1[C:14]1[S:28][C:17]2[C:18]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1.Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[N:12][N:11]=[C:10]1[C:14]1[S:28][C:17]2[C:18]3[CH:26]=[CH:25][C:24]([NH:27][C:30](=[O:31])[O:32][CH3:33])=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 66899984HCID 66899984, compound

Product 1

HCID 44242164HCID 44242164, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-(2-chlorophenyl)-4H-1,2,4-triazol-3-yl)-4,5-dihydro-benzo[b]thieno[2,3-d]oxepin-8-amine HCl salt (0.2 g, 0.464 mmol) in 10 ml of dried DCM was added TEA (0.32 mL, 2.3 mmol). The mixture was stirred at 0° C. for 20 min and 0.2 ml of methyl chloroformate was added. The reaction mixture was stirred for 10 min and the solution was quenched with water and evaporated to the crude product, which was purified by preparative HPLC to give 113 (81 mg, 38%). 1HNMR (DMSO-d6, 400 MHz): δ 9.78 (s, 1H), 8.81 (s, 1H), 7.79-7.12 (m, 7H), 6.53 (s, 1H), 4.15 (t, J=5.2 Hz, 2H), 3.63 (s, 3H), 2.93 (t, J=5.2 Hz, 2H). MS: (ESI+) 453.1

Workup

  1. stirringThe reaction mixture was stirred for 10 min
  2. customthe solution was quenched with water
  3. customevaporated to the crude product, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-ce50d9841f934e98895b4f009df7cdba
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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