Ammonia → HCID 59447976, compound

HRID 1916296Notes

Reaction equation

HRID 1916296 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[C:28]3[C:27]4[C:22](=[CH:23][C:24]([C:29]([OH:31])=O)=[CH:25][CH:26]=4)[NH:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:32]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[C:28]3[C:27]4[C:22](=[CH:23][C:24]([C:29](=[O:31])[NH2:32])=[CH:25][CH:26]=4)[NH:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59447972HCID 59447972, compound

Product 1

HCID 59447976HCID 59447976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(tert-Butoxycarbonylamino-methyl)-morpholin-4-yl]-9H-pyrimido[4,5-b]indole-7-carboxylic acid (6 mg, 0.014 mmol) was stirred in DMF (0.25 mL) at 0° C. Carbonydiimidazole (2.5 mg, 0.016 mmol) was added and the reaction allowed to proceed to room temperature for 30 minutes. Ammonia (28% aqueous, 0.04 mL) was added. The reaction mixture was concentrated to dryness and then the reaction was repeated to afford a complete conversion. The reaction mixture was concentrated to give the title compound as a yellow solid (5 mg, 0.012 mmol), which was deprotected without further purification. LC-MS (1) Rt 1.48 min; m/z 427 (ES+).

Workup

  1. additionCarbonydiimidazole (2.5 mg, 0.016 mmol) was added
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customto afford a complete conversion
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c86ec2af947d4209ba7386fe7cdd9d28
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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