Dimethylamine, hydrochloride → HCID 69039225, compound

HRID 1766105Notes

Reaction equation

HRID 1766105 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)C(C)C)(C)C.[C:14]([NH:18][C:19]([C:21]1[S:54][C:24]2[N:25]=[C:26]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:27]=[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36]([O:38]C4C=CC([N+]([O-])=O)=CC=4)=O)[CH:30]=3)[C:23]=2[C:22]=1[NH2:55])=[O:20])([CH3:17])([CH3:16])[CH3:15]>ClCCl>[C:14]([NH:18][C:19]([C:21]1[S:54][C:24]2[N:25]=[C:26]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:27]=[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36]([N:3]([CH3:4])[CH3:2])=[O:38])[CH:30]=3)[C:23]=2[C:22]=1[NH2:55])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 69037811HCID 69037811, compound

Product 1

HCID 69039225HCID 69039225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl amine hydrochloride (150 mg) was added to a solution of N,N-diisopropylethylamine (DIPEA, 0.50 ml) and tert-butyl 5-amino-2-phenyl-4-(3-(p-nitro-phenoxycarbonylamino)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 31(h), 250 mg) in dichloromethane (5 ml) and the reaction mixture was stirred at room temperature overnight. Subsequently, the reaction mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was concentrated under reduced pressure. The title compound was purified by HPLC using a Luna C-18 column with the following gradient: H2O/CH3CN=80/20 to 0/100 (v/v) in 45 min. The title compound was then lyophilized from a mixture of 1,4-dioxane and H2O.

Workup

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe title compound was purified by HPLC
  4. waitH2O/CH3CN=80/20 to 0/100 (v/v) in 45 min
  5. additionThe title compound was then lyophilized from a mixture of 1,4-dioxane and H2O

Sources & evidence

ORD record
ord-ba50c0b3b0624c289ecc29b15d5ed8e1
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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