Diisopropylethylamine → HCID 76601340, compound

HRID 1174893Notes

Reaction equation

HRID 1174893 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:4]1.[C:19]1([C:25]2[O:29][N:28]=[C:27]([C:30](O)=[O:31])[CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([NH:17][C:30]([C:27]4[CH:26]=[C:25]([C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[O:29][N:28]=4)=[O:31])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1519165-Phenyl-3-isoxazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 76601340HCID 76601340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (0.100 g, 0.381 mmol) (Example 1, step 3), dissolved in CH2Cl2 (5.0 mL), with 5-phenyl-isoxazole-3-carboxylic acid (0.079 g, 0.419 mmol), HATU (0.145 g, 0.381 mmol), and DIEA (0.20 mL, 1.14 mmol) in a 40 mL reaction vial and shake the mixture overnight at 40° C. Dilute the mixture with CH2Cl2 (25 mL) and wash with 1.0 M NaOH (25 mL) which results in emulsions forming. Wait 3 h for the emulsions to disappear, separate the layers and dry the organic portion over sodium sulfate. Filter and concentrate in vacuo to yield the compound as a yellow solid. Purify using silica gel chromatography (5% MeOH/CH2Cl2) to afford the title compound as a yellowish-white solid (117 mg, 71%). mass spectrum (m/e): 434.2 [M+1], 432.2 [M−1]. 1H NMR (400 MHz, DMSO-d6): δ10.76 (s, 1H), 8.27 (d, 1H, J=2 Hz), 7.98 (m, 2H), 7.56-7.63 (m, 4H), 7.49 (s, 1H), 7.45 (d, 1H, J=8.8 Hz), 3.73 (t, 1H, J=9.2 Hz), 3.64 (t, 1H, J=9.2 Hz), 3.49 (m, 1H), 3.29 (m, 1H), 2.90 (m, 1H), 2.21 (s, 6H), 2.19 (m, 1H), 1.91 (m, 1H).

Workup

  1. customthe mixture overnight
  2. customat 40° C
  3. washwash with 1.0 M NaOH (25 mL) which
  4. customresults in emulsions
  5. customforming
  6. customseparate the layers
  7. dry with materialdry the organic portion over sodium sulfate
  8. filtrationFilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a3752b0f370644a48fa051356e5de5c8
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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