Diisopropylethylamine → HCID 178422770, compound

HRID 1898390Notes

Reaction equation

HRID 1898390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:63][C:64]1[CH:69]=[CH:68][C:67]([C:70]([F:73])([F:72])[F:71])=[CH:66][N+:65]=1[O-]>[Fe].C(O)(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:63][C:64]3[CH:69]=[CH:68][C:67]([C:70]([F:72])([F:71])[F:73])=[CH:66][N:65]=3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178422815HCID 178422815, compoundHCID 178507581HCID 178507581, compound

Product 1

HCID 178422770HCID 178422770, compoundYield 8.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by following the procedure described for Example-121 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.100 g, 0.266 mmol), COMU (0.284 g, 0.663 mmol), DIPEA (0.085 g, 0.658 mmol), 2-amino-5-(trifluoromethyl)pyridine 1-oxide (Intermediate-41, 0.052 g, 0.292 mmol), DMF (5 mL), iron powder (0.100 g) and acetic acid (5.0 mL) to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.12 (s, 2H), 7.33 (m, 3H), 7.54 (s, 1H), 8.23 (d, J=8.7 Hz, 1H), 8.48 (d, J=8.70 Hz, 1H), 8.57 (s, 1H), 10.47 (s, 1H), 11.00-12.00 (s, 2H); MS [M]+: 520.18.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d931659e0f4149799aa655bfa15333bc
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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