Triethylamine → HCID 24890243, compound

HRID 1469939Notes

Reaction equation

HRID 1469939 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[S:10][C:9](=[NH:11])[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1.[CH2:19]1[CH:26]2[C:22]3([C:28](O)=[O:29])[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[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[S:10][C:9](=[N:11][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:29])[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66860376HCID 66860376, compound

Product 1

HCID 24890243HCID 24890243, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 45A (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 (400 MHz, DMSO-d6) δ 1.50-1.61 (m, 4H), 1.65-1.76 (m, 4H), 2.03-2.11 (m, 2H), 2.21-2.26 (m, 2H), 2.48-2.55 (m, 1H), 3.25 (s, 3H), 3.68 (t, J=5.4 Hz, 2H), 3.99 (s, 2H), 4.25 (t, J=5.4 Hz, 2H), 7.03-7.13 (m, 3H), 7.26 (s, 1H), 7.33-7.41 (m, 1H); MS (DCI/NH3) m/z 415 (M+H)+.

Sources & evidence

ORD record
ord-b8fdb5e2d1c84e42a4646ac612e06ed4
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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