Hydrochloric Acid → 3-(Benzyloxy)-5-bromo-N-(4-(piperidin-4-yl)thiazol-2-yl)pyridin-2-amine dihydrochloride

HRID 1426155Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]([NH2:19])=[S:18])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:28][C:29]([CH:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]1)=O.[ClH:44]>>[ClH:44].[ClH:44].[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:28]=[C:29]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[N:19]=2)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 8471Triethylamine

HCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

HCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

Product 1

HCID 866396943-(Benzyloxy)-5-bromo-N-(4-(piperidin-4-yl)thiazol-2-yl)pyridin-2-amine dihydrochlorideYield 51.4%

Procedure

1-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea (200 mg, 0.59 mmol), triethylamine (0.144 ml, 1.03 mmol) and tert-butyl 4-(2-bromoacetyl)piperidine-1-carboxylate (253 mg, 0.82 mmol) were reacted according to the procedure in Example 1, Step D to afford the title compound (157.6 mg, 51.4% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 10.30 (bs, 1H), 8.83 (bs, 1H), 8.60 (bs, 1H), 7.99 (dd, 1H), 7.67 (d, 1H), 7.59 (m, 2H), 7.45-7.33 (m, 3H), 6.75 (s, 1H), 5.30 (s, 2H), 3.32 (d, 2H), 3.05-2.85 (m, 3H), 2.11 (d, 2H), 1.79 (m, 2H). Mass spectrum (apci) m/z=445.2 (M+H-2HCl).

Sources & evidence

ORD record: ord-fd9b0c01aa5b481d901b46fa8426520b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933077B2

Reaction notes

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