Cyanamide → HCID 178492299, compound

HRID 2230093Notes

Reaction equation

HRID 2230093 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)=S)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1CCC([N:40]=[C:41]=[N:42]C2CCCCC2)CC1.C(N(CC)C(C)C)(C)C.N#CN>C(#N)C>[C:41]([N:42]=[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)[NH:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:40]

Participants

6

Reactant 4

HCID 9864Cyanamide2×HCID 10868Dicyclohexylcarbodiimide2×HCID 81531Diisopropylethylamine2×HCID 11730369HCID 11730369, compound

Product 1

HCID 178492299HCID 178492299, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution (15 mL) of N-(3,4-dimethoxyphenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinethiocarboxamide (499 mg, 1.07 mmol) described in WO 98/14431, DCC (4397 mg, 2.13 mmol), N,N-diisopropylethylamine (Hünig base) (0.19 mL, 1.09 mmol) and cyanamide (224 mg, 5.32 mmol) were added, followed by heating under reflux in argon atmosphere for 2 days. DCC (439 mg, 2.13 mmol), Hünig base (0.19 mL, 1.09 mmol) and cyanamide (224 mg, 5.32 mmol) were further added thereto, followed by heating under reflux for 2 days. After the reaction solution was concentrated, the resulting residue was purified by silica gel column chromatography to give the target compound (167 mg, 0.35 mmol).

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux in argon atmosphere for 2 days
  4. temperatureby heating
  5. temperatureunder reflux for 2 days
  6. concentrationAfter the reaction solution was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11896da0c59149da92d694f0d093b6d3
Source dataset
uspto-grants-2002_07
Patent number
US06423716B1

Reaction notes

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