Hydrochloric Acid → 4-(9-cyclohexyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid

HRID 2111325Notes

Reaction equation

HRID 2111325 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][N:7]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[N:19]=1.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[O:30][CH3:31].Cl>>[CH:13]1([N:7]2[CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]3[CH:4]=[N:3][C:2]([NH:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=4[O:30][CH3:31])=[N:19][C:6]2=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2880572486-69-3HCID 866175922-Chloro-9-cyclohexyl-5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 581539254-(9-cyclohexyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acidYield 64.2%

Procedure

A mixture of 0.25 g (0.00089 mole) of 2-chloro-9-cyclohexyl-5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one (VI-20), 0.0022 g (0.0013 mole) of 4-amino-3-methoxybenzoic acid and 3 mL of 1 M hydrochloric acid was heated in a sealed vial at 100 degrees for 1.5 hours. After cooling, the solid was collected by filtration to give 0.235 g of 4-(9-cyclohexyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-28a).

Workup

  1. temperaturewas heated in a sealed vial at 100 degrees for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-a17d18f6116a45e28a7bbd12c5bbd56a
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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