3-Chloro-4-(3-fluorobenzyloxy)aniline → Ethyl 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5,7-dihydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylate

HRID 38528Notes

Reaction equation

HRID 38528 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)[NH2:23]>>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:3]3[C:10]4[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1

Participants

3

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 58116864Ethyl12-chloro-7-thia-4,9,11-triazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),9,11-tetraene-4-carboxylate

Product 1

HCID 58116877Ethyl 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5,7-dihydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylateYield 65%

Procedure

In analogy to Example 22A, the title compound was prepared from ethyl 4-chloro-5,7-dihydro-6H-pyrrolo[3′,4′:4,5]thieno[2,3-d]pyrimidine-6-carboxylate from Example 21A (100 mg, 0.35 mmol) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline from Example 4A (93 mg, 0.37 mmol) to give 157 mg (72% purity, 65% yield), which was used in the next step without purification.

Workup

  1. customto give 157 mg (72% purity, 65% yield), which
  2. customwas used in the next step without purification

Sources & evidence

ORD record
ord-594468d559704b868d2e46c6f7f82eb2
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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