Triethylamine → (S)-6-oxo-1,6-dihydro-pyridazine-4-carboxylic acid (3-{[5-(4-chloro-2-trifluoromethyl-phenylamino)-3-fluoro-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-amide

HRID 1396497Notes

Reaction equation

HRID 1396497 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]([NH:10][C@@:11]2([C:16]([OH:18])=O)[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])=[CH:3]1.[NH2:19][CH2:20][C:21]1[N:26]=[CH:25][C:24]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[C:35]([F:38])([F:37])[F:36])=[CH:23][C:22]=1[F:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:24]2[CH:23]=[C:22]([F:39])[C:21]([CH2:20][NH:19][C:16]([C@:11]3([NH:10][C:8]([C:4]4[CH:5]=[N:6][NH:7][C:2](=[O:1])[CH:3]=4)=[O:9])[CH2:15][CH2:14][O:13][CH2:12]3)=[O:18])=[N:26][CH:25]=2)=[C:29]([C:35]([F:37])([F:38])[F:36])[CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59496210(6-Aminomethyl-5-fluoro-pyridin-3-yl)-(4-chloro-2-trifluoromethyl-phenyl)-amineHCID 59496525(S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid

Product 1

HCID 56649697(S)-6-oxo-1,6-dihydro-pyridazine-4-carboxylic acid (3-{[5-(4-chloro-2-trifluoromethyl-phenylamino)-3-fluoro-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid (144.7 mg, 0.40 mmol), (6-aminomethyl-5-fluoro-pyridin-3-yl)-(4-chloro-2-trifluoromethyl-phenyl)-amine (127.9 mg, 0.40 mmol), TBTU (154 mg), triethylamine (0.112 mL) and DMF (1.0 mL) in 7 mL THF was stirred for 3 hours at ambient temperature. Then the mixture was evaporated down and the crude product thus obtained was purified by column chromatography (RP, column: YMC-Pack ODS-AQ, 5 μM).

Workup

  1. customThen the mixture was evaporated down

Sources & evidence

ORD record
ord-989f78efe5e849e1ac082c0d4e561cc4
Source dataset
uspto-grants-2014_12
Patent number
US08901127B2

Reaction notes

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