Triethylamine → HCID 59140924, compound

HRID 737205Notes

Reaction equation

HRID 737205 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:39]1([C:42](Cl)=[O:43])[CH2:41][CH2:40]1>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:42]([CH:39]3[CH2:41][CH2:40]3)=[O:43])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 59009442HCID 59009442, compound2×

Product 1

HCID 59140924HCID 59140924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-[4-(4-Aminomethyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5379, Example 379, 100 mg, 0.23 mmol) was dissolved in 5 mL of dry CH2Cl2. To this solution at 0° C. was added triethylamine (0.035 mL, 0.46 mmol) followed by cyclopropanecarbonyl chloride (48 mg, 0.46 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then quenched using H2O. The organic phase was isolated and evaporated under reduced pressure to yield the crude product, which was then purified using reverse phase HPLC. MS: 505.2(M+H−); H1 NMR (DMSO-d6): δ(ppm) 12.41 (s, 1H), 8.58 (s, 1H), 7.82 (d, 2H), 7.57 (d, 1H), 7.31 (dd, 4H), 7.10 (dd, 3H), 5.00 (m, 2H), 4.45 (m, 1H), 4.23 (d, 2H), 3.48 (m, 2H), 2.21 (m, 1H), 1.89 (m, 3H), 1.60 (m, 1H), 0.60 (d, 4H).

Workup

  1. customquenched
  2. customThe organic phase was isolated
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-358df5177d814cafa63905720a8af335
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

Loading…