Diisopropylethylamine → HCID 71533438, compound

HRID 2274949Notes

Reaction equation

HRID 2274949 reaction equation
Cl.[F:2][C:3]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]=2[C:8]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[N:7]1.[C:28]([O:32][CH2:33][C:34](O)=[O:35])([CH3:31])([CH3:30])[CH3:29].C(N(CC)C(C)C)(C)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>>[C:28]([O:32][CH2:33][C:34]([N:11]1[CH2:12][CH2:13][C:14]2[N:6]([CH2:5][C:4]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:3]=3[F:2])[N:7]=[C:8]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[C:9]=2[CH2:10]1)=[O:35])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27609982-(Tert-butoxy)acetic acidHCID 131733416HCID 131733416, compound

Product 1

HCID 71533438HCID 71533438, compoundYield 22.6%

Conditions

Temperature
25 °C

Procedure

To a 0° C. cold mixture of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (7c) (0.4 g, 1.142 mmol) and 2-tert-butoxyacetic acid (196 mg, 1.485 mmol) was added N,N-diisopropylethylamine (0.59 g, 4.57 mmol) and TOTU (O-(Cyano(ethoxycarbonyl)methylenamino)-1,1,3,3-tetramethyluronium tetrafluoroborate, 562 mg, 1.71 mmol) and the mixture was stirred at 25° C. for 1 h. The crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 120 mg of 3-[5-(2-tert-Butoxy-acetyl)-1-(2,4-difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8d).

Workup

  1. customThe crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-ae60a881a93340169405c3bb1e6b23ff
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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