2-Amino-6-methoxybenzothiazole → HCID 46927440, compound

HRID 592129Notes

Reaction equation

HRID 592129 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([NH2:26])[S:25][C:21]=2[CH:20]=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>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([NH:26][C:14](=[O:16])[CH2:13][C:10]3[CH:9]=[CH:8][C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[CH:12][CH:11]=3)[S:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 156302-Amino-6-methoxybenzothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21091633[4-(Pyridin-4-yl)phenyl]acetic acid

Product 1

HCID 46927440HCID 46927440, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(4-(pyridin-4-yl)phenyl)acetic acid 3-1 (45 mg, 0.21 mmol), 6-methoxybenzo[d]thiazol-2-amine 3-2 (36 mg, 0.20 mmol), and DIEA (32 mg, 0.25 mmol) in DMF (0.5 mL) under stiffing was added HATU (84 mg, 0.22 mmol). The solution was stirred for 2 hours before it was subject to reverse phase HPLC for purification to give compound 3 as white solid. MS m/z 376.1 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 12.60(s, 1H), 8.70(m, 2H), 7.87(m, 2H), 7.78(m, 2H), 7.72(d, 1H, J=8.8 Hz), 7.63(d, 1H, J=2.8 Hz), 7.58(m, 2H), 7.11(dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 3.96(s, 2H), 3.86(s, 3H).

Workup

  1. customfor purification

Sources & evidence

ORD record
ord-33729fc21a1f4b57a7695b5c4f61cb0f
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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