4,5,6,7-Tetrahydro[1,3]thiazolo[5,4-c]pyridine--hydrogen chloride (1/1) → HCID 60197704, compound

HRID 587177Notes

Reaction equation

HRID 587177 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1.Cl.[N:21]1[C:29]2[CH2:28][CH2:27][NH:26][CH2:25][C:24]=2[S:23][CH:22]=1>>[N:21]1[C:29]2[CH2:28][CH2:27][N:26]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]4[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=4)[N:3]=3)[CH2:25][C:24]=2[S:23][CH:22]=1

Participants

3

Reactant 2

HCID 568461694,5,6,7-Tetrahydro[1,3]thiazolo[5,4-c]pyridine--hydrogen chloride (1/1)HCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Product 1

HCID 60197704HCID 60197704, compound

Procedure

B45 was prepared following the general procedure reported for B10 using A1 and 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine hydrochloride. The title compound (B45) was purified by column chromatography (silica gel, DCM/MeOH gradient 100:0 to 85:15); yield: 28.9 mg (7%), colorless amorphous solid. 1H NMR (400 MHz, d6-DMSO, 300K) δ 2.84-2.94 (m, 2H), 4.13 (t, J=5.8 Hz, 2H), 4.23 (s, 2H), 5.03 (s, 2H), 6.83 (s, 2H), 7.00 (d, J=7.1 Hz, 1H), 7.29 (t, J=7.7 Hz, 1H), 7.42-7.63 (bm, 1H), 7.82-7.93 (bm, 1H), 8.28 (s, 1H), 8.96 (s, 1H), 9.77 (s, 1H). MS (ES) C16H17N7O2S2 requires: 403. found: 404 (M+H)+.

Workup

  1. customB45 was prepared
  2. customThe title compound (B45) was purified by column chromatography (silica gel, DCM/MeOH gradient 100:0 to 85:15)

Sources & evidence

ORD record
ord-188bdbf933194cfba55ad0fce3768d1a
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

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