5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 74983227, compound

HRID 1915927Notes

Reaction equation

[CH:1]1([N:4]2[C:8]([N:9]3[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH:12]([NH:18]C(=O)OC(C)(C)C)[CH2:11][CH2:10]3)=[C:7]([N+:26]([O-])=O)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.C(OC([NH:36][C:37]1[S:41][C:40]([C:42]2[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:43]=2[F:49])=[N:39][C:38]=1[C:50](O)=[O:51])=O)(C)(C)C>>[NH2:36][C:37]1[S:41][C:40]([C:42]2[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:43]=2[F:49])=[N:39][C:38]=1[C:50]([NH:26][C:7]1[CH:6]=[N:5][N:4]([CH:1]2[CH2:2][CH2:3]2)[C:8]=1[N:9]1[CH2:15][CH2:14][C@@H:13]([O:16][CH3:17])[C@@H:12]([NH2:18])[CH2:11][CH2:10]1)=[O:51]

Participants

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

HCID 86680127HCID 86680127, compound

Product 1

HCID 74983227HCID 74983227, compoundYield 23%

Procedure

Following the procedure for Example 101 starting from tert-butyl 1-(1-cyclopropyl-4-nitro-1H-pyrazol-5-yl)-5-methoxyazepan-4-ylcarbamate and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxylic acid gave 386 as an off-white solid (29 mg, 23% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.96 (s, 1H), 7.86 (s, 1H), 7.36-7.28 (m, 1H), 7.02 (t, J=8.9 Hz, 2H), 6.19-6.10 (m, 2H), 3.50-3.35 (m, 4H), 3.33 (s, 3H), 3.25-3.11 (m, 2H), 2.19-2.05 (m, 1H), 2.03-1.96 (m, 1H), 2.01-1.60 (m, 2H), 1.57 (s, 3H), 1.27-1.12 (m, 2H), 0.97 (d, J=7.1 Hz, 2H). LCMS (ES+) m/z 504 (M+1)

Sources & evidence

ORD record: ord-2b3fb045941a4355952685e7628f220a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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