1-Hydroxybenzotriazole → HCID 9958620, compound

HRID 131252Notes

Reaction equation

HRID 131252 reaction equation
Cl.[CH3:2][N:3]([CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.Cl.[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][CH:43]=1)[CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[N:33][C:34]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)=[C:29]2[CH:28]=[N:27]1)[CH3:20].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(Cl)Cl>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][CH:43]=1)[CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[N:33][C:34]([N:35]3[CH2:36][CH2:37][N:38]([C:11](=[O:13])[C:10]4[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][N:3]([CH3:2])[CH3:16])=[CH:15][CH:14]=4)[CH2:39][CH2:40]3)=[C:29]2[CH:28]=[N:27]1)[CH3:20]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131748714-[2-(Dimethylamino)ethoxy]benzoic acid--hydrogen chloride (1/1)HCID 69298924HCID 69298924, compound

Product 1

HCID 9958620HCID 9958620, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To 4-[2-(dimethylamino)ethoxy]benzoic acid hydrochloride (66 mg, compound obtained in Reference example 78(2)) is added successively methylene chloride (2 mL), 1-(3-ethoxybenzyl)-4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride (100 mg), 1-hydroxybenzotriazole (49.3 mg), triethylamine (118.6 μL) and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (70 mg) and the mixture is stirred at room temperature for 17 hours. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The resultant crude product is purified by flash column chromatography on NH-silica gel (Solvent; ethyl acetate:chloroform=1:0→0:1) to give 1-(3-ethoxybenzyl)-4-[4-[4-[2-(dimethylamino)ethoxy]benzoyl]piperazin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine (103 mg, yield; 69%) as an amorphous powder. MS (APCI) m/z: 530 [M+H]+

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. concentrationconcentrated
  4. customThe resultant crude product is purified by flash column chromatography on NH-silica gel (Solvent; ethyl acetate:chloroform=1:0→0:1)

Sources & evidence

ORD record
ord-4ab62b8142ee42588fa9db13a3cdd414
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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