Reaction equation
F[C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:11][C:10](=[NH:12])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)=[CH:4][CH:3]=1.[CH2:19]1[CH:26]2[C:22]3([C:28]([OH:30])=O)[CH2:23][CH:24]([CH2:27][CH:20]1[CH2:21]3)[CH2:25]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:48][P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[F:48][C:17]1[CH:18]=[CH:2][CH:3]=[CH:4][C:5]=1[CH2:6][C:7]1[S:11]/[C:10](=[N:12]\[C:28]([C:22]23[CH2:23][CH:24]4[CH2:27][CH:20]([CH2:19][CH:26]2[CH2:25]4)[CH2:21]3)=[O:30])/[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=1Participants
6
Reactant 4
HCID 8471Triethylamine
HCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 668590705-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amineProduct 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the product of Example 44A (342 mg, 1.29 mmol), hexahydro-2,5-methano-pentalene-3a-carboxylic acid (256 mg, 1.54 mmol), HATU (737 mg, 1.24 mmol) and triethylamine (1.08 mL, 7.74 mmol) in 20 mL of DMF was processed according to the method of Example 43B to afford the title compound: 1H NMR (500 MHz, DMSO-d6) δ 1.51-1.61 (m, 4H) 1.65-1.74 (m, 4H) 2.07 (d, J=9.2 Hz, 2H) 2.22-2.26 (m, 2H) 2.51-2.53 (m, 1H) 3.24 (s, 3H) 3.66 (t, J=5.3 Hz, 2H) 3.98 (s, 2H) 4.23 (t, J=5.3 Hz, 2H) 7.16-7.22 (m, 3H) 7.23 (s, 1H) 7.29-7.38 (m, 2H); MS (DCI/NH3) m/z 415 (M+H)+.
Sources & evidence
- ORD record
- ord-346f5172dcbd4ca6a6285f9167ffd75e
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006275B2
Linked notes
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