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Diisopropylethylamine → 2-bromo-6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid

HRID 1014513
Notes
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Reaction equation

HRID 1014513 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[C:24]=1[C:25]([OH:27])=[O:26].C(N(C(C)C)C(C)C)C>CC(O)C>[Br:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:23]([NH:22][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[C:24]=1[C:25]([OH:27])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 105606492-Amino-6-bromobenzoic acidHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 251499842-bromo-6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acidYield 49.2%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (2 g, 5.84 mmols), 2-amino-6-bromobenzoic acid (2.53 g, 11.69 mmols), and N-ethyl-N-(1-methylethyl)-2-propanamine (7.55 g, 58.4 mmols) in 2-propanol (150 ml) was heated at 90° C. for 5 days. The solvent was removed, residue redissolved in DCM (150 ml), washed with 1M HCl(100 ml), organic layer separated, adsorbed onto silica gel, and purified by silica gel chromatography (DCM to 10% MeOH/DCM). The crude product was then recrystallized from ethyl acetate/hexanes to obtain 2-bromo-6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid (1.5 g, 49%). ESIMS (M+H)+=521.

Workup

  1. customThe solvent was removed
  2. dissolutionresidue redissolved in DCM (150 ml)
  3. washwashed with 1M HCl(100 ml), organic layer
  4. customseparated
  5. custompurified by silica gel chromatography (DCM to 10% MeOH/DCM)
  6. customThe crude product was then recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-71ef3951ff694336b148e2bccfdcffde
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981903B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes