Triethylamine → HCID 13036382, compound

HRID 1703174Notes

Reaction equation

HRID 1703174 reaction equation
[N:1]1([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.C(N(CC)CC)C>C(O)CCC>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119872-ChlorobenzothiazoleHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 13036382HCID 13036382, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 2-(1-piperazinyl)-4-amino-6,7-dimethoxy-quinazoline (1.96 g), 2-chlorobenzthiazole (1.02 g), triethylamine (1.82 g) in butanol (100 ml) was refluxed for 72 hr and filtered. The precipitate was taken up in a solution of methanol and dimethyl sulfoxide, and IN sodium hydroxide was added until the mixture was alkaline. The precipitate was collected, washed with water, dried (1.3 g) and crystallized from methanol to give the title compound: mp 242°-245° C.; ir (nujol) 3460 and 3370 cm-1 : uv max (MeOH) 227 (ε=4130), 250 (ε=5280), 276 (ε=3649) and 340 nm (ε=690); nmr (DMSO-d6) δ 3.65 (m, 4H), 3.9 (m, 4H), 3.85 (s, 3H), 3.93 (s, 3H), 5.2 (s, 2H) and 7.2 (m, 6H); and Anal. Calcd for C21H22N6O2S.CH3OH: C, 58.14% H, 5.72% N, 18.50% and Found: C, 57.88% H, 5.90% N, 18.47%.

Workup

  1. temperaturewas refluxed for 72 hr
  2. filtrationfiltered
  3. additionIN sodium hydroxide was added until the mixture
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried (1.3 g)
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-44a47055439f45b68a73cff8548c7038
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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