2-Aminothiazole → 6-(Isoquinolin-5-yl)-N-(1,3-thiazol-2-yl)naphthalene-1-carboxamide

HRID 908328Notes

Reaction equation

HRID 908328 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:21]([OH:23])=O)=[CH:16][CH:15]=[CH:14]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:21]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])=[CH:16][CH:15]=[CH:14]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58828852HCID 58828852, compound

Product 1

HCID 588288896-(Isoquinolin-5-yl)-N-(1,3-thiazol-2-yl)naphthalene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-(isoquinolin-5-yl)-1-naphthoic acid (55 mg, 0.18 mmol), 2-aminothiazole (24 mg, 0.23 mmol), DIPEA (0.048 mL, 0.27 mmol) and HATU (0.1 g, 0.27 mmol) were stirred in CHCl3 (1 mL) at room temperature overnight. The solid formed was filtered, rinsed with CHCl3, MeOH and dried under vacuum to give the titled compound as a solid. MS (ESI pos. ion) m/z: 382. (M+H). Calc'd Exact Mass for C23H15N3OS: 381.

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washrinsed with CHCl3, MeOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ae68d2277459425dba88aad393badcca
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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