Triethylamine → HCID 89610494, compound

HRID 1507699Notes

Reaction equation

HRID 1507699 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:21][C:22]1[C:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:25]([C:35]([NH2:37])=O)[N:24]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:23]=1[C:46]([N:48]([CH3:50])[CH3:49])=[O:47])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([O:21][C:22]1[C:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:25]([C:35]#[N:37])[N:24]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:23]=1[C:46]([N:48]([CH3:49])[CH3:50])=[O:47])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 89610489HCID 89610489, compound

Product 1

HCID 89610494HCID 89610494, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (27.0 μL, 0.19 mmol) was added dropwise to a stirred solution of 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-N2,N2-dimethyl-1H-pyrrole-2,5-dicarboxamide (11) (88 mg, 0.18 mmol) and triethylamine (74.3 μL, 0.53 mmol) in DCM (4 mL) at 0° C. The reaction mixture was stirred for 1 h before and trifluoroacetic anhydride (27.0 μL, 0.19 mmol) was added and the mixture allowed to warm to RT. The reaction was partitioned between sat. NaHCO3 (aq.) (5 mL) and DCM (5 mL) the organic layer was separated and volatiles removed in vacuo to afford 4-bis(benzyloxy)-5-cyano-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (12) (85 mg, 100%), as a yellow oil: m/z 482 (M+H)+ (ES+).

Workup

  1. additionwas added
  2. customThe reaction was partitioned between sat. NaHCO3 (aq.) (5 mL) and DCM (5 mL) the organic layer
  3. customwas separated
  4. customvolatiles removed in vacuo

Sources & evidence

ORD record
ord-aae683fd6eeb407b99585ad29ade6840
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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