Triethylamine → HCID 140504888, compound

HRID 1725179Notes

Reaction equation

HRID 1725179 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([CH2:23][C:24](O)=[O:25])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[N:40]1([C:45]([NH2:47])=[NH:46])[CH:44]=[CH:43][CH:42]=[N:41]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([CH2:23][C:24](=[O:25])[NH:47][C:45](=[NH:46])[N:40]3[CH:44]=[CH:43][CH:42]=[N:41]3)[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 57423718HCID 57423718, compound

Product 1

HCID 140504888HCID 140504888, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 120 mg pyrrolyl acetic acid from Step 4 was added 97 mg (0.6 mmol, 5 equiv.) of carbonyldiimidazole and 2 mL CH2Cl2. The reaction was mixed at room temperature for one hour, upon which time was added 88 mg (5 equiv.) 1H-pyrazole-1-carboxamidine hydrochloride, 0.16 mL (10 equiv.) triethylamine, and a catalytic amount of 4-dimethylaminopyridine. The reaction was mixed at room temperature for one hour, filtered to remove any precipitates formed, and washed with water. The organic phase was separated from the aqueous phase and concentrated to afford 59 mg crude N-ethyl-4-(1-{[(imino-pyrazol-1-yl-methyl)-carbamoyl]-methyl}-5-phenyl-1H-pyrrol-2-yl)-benzamide, which was used in the next step without purification.

Workup

  1. additionThe reaction was mixed at room temperature for one hour, upon which time
  2. additionThe reaction was mixed at room temperature for one hour
  3. filtrationfiltered
  4. customto remove any precipitates
  5. customformed
  6. washwashed with water
  7. customThe organic phase was separated from the aqueous phase
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b31821808cb64cc89c088f8c9e2a54da
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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