Reaction equation
Br.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]1=[NH:15].[CH2:16]1[CH:23]2[C:19]3([C:25](O)=[O:26])[CH2:20][CH:21]([CH2:24][CH:17]1[CH2:18]3)[CH2:22]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8]/[C:7]/1=[N:15]\[C:25]([C:19]12[CH2:20][CH:21]3[CH2:24][CH:17]([CH2:16][CH:23]1[CH2:22]3)[CH2:18]2)=[O:26]Participants
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 668590283-(2-methoxy-ethyl)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylideneamine hydrobromideProduct 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the product of Example 68A (293 mg, 1.00 mmol), hexahydro-2,5-methano-pentalene-3a-carboxylic acid (199 mg, 1.20 mmol), HATU (570 mg, 1.50 mmol) and triethylamine (836 mL, 6.00 mmol) in 15 mL of DMF was processed according to the method of Example 3B to afford the title compound: 1H NMR (500 MHz, DMSO-d6) δ 1.53-1.62 (m, 4 H) 1.67-1.82 (m, 8 H) 2.07-2.12 (m, 2 H) 2.23-2.27 (m, 2 H) 2.45-2.49 (m, 3 H) 2.54-2.59 (m, 2 H) 3.23 (s, 3 H) 3.63 (t, J=5.3 Hz, 2 H) 4.16 (t, J=5.5 Hz, 2 H); MS (DCI/NH3) m/z 361 (M+H)+.
Sources & evidence
- ORD record
- ord-effb1b483e274e5ca4fba9500e2f1d6d
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875639B2
Linked notes
Loading…