Triethylamine → HCID 24890243, compound

HRID 255059Notes

Reaction equation

HRID 255059 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, 4 H), 1.65-1.76 (m, 4 H), 2.03-2.11 (m, 2 H), 2.21-2.26 (m, 2 H), 2.48-2.55 (m, 1 H), 3.25 (s, 3 H), 3.68 (t, J=5.4 Hz, 2 H), 3.99 (s, 2 H), 4.25 (t, J=5.4 Hz, 2 H), 7.03-7.13 (m, 3 H), 7.26 (s, 1 H), 7.33-7.41 (m, 1 H); MS (DCI/NH3) m/z 415 (M+H)+.

Sources & evidence

ORD record
ord-73d66c625a4e45e78ba73d306232f34d
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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