2-Chloroethyl chloroformate → HCID 57814714, compound

HRID 521637Notes

Reaction equation

HRID 521637 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.Cl[C:38]([O:40][CH2:41][CH2:42][Cl:43])=[O:39]>>[Cl:43][CH2:42][CH2:41][O:40][C:38](=[O:39])[NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 123052-Chloroethyl chloroformateHCID 81531DiisopropylethylamineHCID 46833678N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide

Product 1

HCID 57814714HCID 57814714, compoundYield 38%

Procedure

To a solution of N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide (0.5000 g, 1.365 mmol) and N,N-Diisopropylethylamine (0.2383 mL, 1.365 mmol) in 1 mL of was added dropwise, 2-Chloroethyl chloroformate (0.1951 g, 1.365 mmol). The reaction mixture was stirred overnight at ambient temperature. Ethanol was removed under vacuum and the crude was purified by preparative LCMS (m/z=472). The proper fractions were collected and lyophilized to afford the title compound as an off-white solid in 38% yield. LCMS m/z (%)=472 (M+H 35Cl, 100), 474 (M+H 37Cl, 40). 1H NMR (400 MHz, CDCl3) δ 8.16 (s, 1H), 7.71 (d, J=2.16 Hz, 1H), 7.68 (d, J=2.01 Hz, 1H), 7.45-7.34 (m, 3H), 7.08 (d, J=8.08 Hz, 1H), 6.98 (d, J=8.08 Hz, 1H), 6.31 (bs, 1H), 7.19-7.13, (m, 2H), 5.18 (bt, J=5.80 Hz, 1H), 4.28 (t, J=6.01 Hz, 2H), 4.03 (t, J=4.80 Hz, 2H), 3.85 (s, 3H), 3.78 (s, 3H), 3.65 (t, J1=5.80 Hz, 2H), 3.45 (q, J=11.10 Hz, 2H).

Workup

  1. customEthanol was removed under vacuum
  2. customthe crude was purified by preparative LCMS (m/z=472)
  3. customThe proper fractions were collected

Sources & evidence

ORD record
ord-8b27339eaf6a4a50ae2d991cb29d89fd
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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