Diisopropylethylamine → N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)-2-(pyridin-2-yl)acetamide

HRID 2077535Notes

Reaction equation

HRID 2077535 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:18][CH:19]([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.[N:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[CH2:62][C:63](O)=[O:64]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:63](=[O:64])[CH2:62][C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][N:56]=4)[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:18][CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575849166-(6-Chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine

Product 1

HCID 57585001N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)-2-(pyridin-2-yl)acetamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (121.8 mg, 0.382 mmol) and HATU (215.9 mg, 0.568 mmol) were suspended in DCM (2.9 ml) and diisopropylethylamine (0.21 ml, 1.2 mmol) and 2-pyridylacetic acid hydrochloride (94.3 mg, 0.543 mmol) were added. The reaction was stirred under nitrogen at room temperature overnight, concentrated and purified on a silica gel column (20:1 DCM/MeOH). Fractions with product were collected, concentrated, and purified on HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes). Fractions with product were collected, concentrated, and dried under high vacuum in a water bath (˜50° C.), then at room temperature overnight to afford N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)-2-(pyridin-2-yl)acetamide (57.5 mg, 34% yield). MS (ESI pos. ion) m/z: 438. Calculated exact mass for C22H20ClN5OS 437.

Workup

  1. concentrationconcentrated
  2. custompurified on a silica gel column (20:1 DCM/MeOH)
  3. customFractions with product were collected
  4. concentrationconcentrated
  5. custompurified on HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes)
  6. customFractions with product were collected
  7. concentrationconcentrated
  8. customdried under high vacuum in a water bath (˜50° C.)

Sources & evidence

ORD record
ord-066271fe2d1841c5a3d6f07e0206fb33
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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