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Carbon Dioxide → N'-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine

HRID 1842675
Notes
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Reaction equation

HRID 1842675 reaction equation
[OH-].[Na+].C1(S([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[C:26]([Cl:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]4[CH:30]=[C:31]([NH2:44])[C:32]([C:37]5[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH:42]=5)=[CH:33][C:34]=4[O:35][CH3:36])[N:22]=3)=[CH:13]2)(=O)=O)C=CC=CC=1.C(=O)=O>CO>[Cl:27][C:26]1[C:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][CH:13]=2)=[N:22][C:23]([NH:28][C:29]2[CH:30]=[C:31]([NH2:44])[C:32]([C:37]3[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH:42]=3)=[CH:33][C:34]=2[O:35][CH3:36])=[N:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 86677326N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine2×

Product 1

HCID 86677231N'-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamineYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (2M, 1.488 mL, 2.98 mmol) was added in one portion to a mixture of N′-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine (Intermediate 8, 283 mg, 0.47 mmol) in CH3OH (6 mL) at r.t. under N2. The resulting solution was stirred at reflux for 0.5 h. Dry ice was then added and the resulting mixture was concentrated in vacuo. The resulting residue was triturated with CH2Cl2/CH3OH (4:1, 20 mL), filtered and the filtrate was concentrated in vacuo to give a residue. Purification by FCC, eluting with 2-10% methanolic ammonia in CH2Cl2 gave the title compound (102 mg, 47%) as a pale yellow powder; 1H NMR: 2.30 (3H, s), 2.41 (2H, s), 2.60 (2H, t), 3.02 (2H, d), 3.70 (3H, s), 4.27 (2H, s), 5.73 (1H, s), 6.65 (1H, s), 7.08 (1H, t), 7.17-7.23 (1H, m), 7.26 (1H, s), 7.48 (1H, d), 8.18 (1H, s), 8.38 (1H, s), 8.41 (1H, d), 8.49 (1H, s), 11.85 (1H, s); m/z: ES+ MH+ 460.

Workup

  1. temperatureat reflux for 0.5 h
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe resulting residue was triturated with CH2Cl2/CH3OH (4:1, 20 mL)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a residue
  7. customPurification by FCC
  8. washeluting with 2-10% methanolic ammonia in CH2Cl2

Sources & evidence

ORD record
ord-9de4368fe987421f8c4e87b502ebd42a
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946235B2

Reaction notes

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