Ethyl isocyanate → HCID 89444146, compound

HRID 574651Notes

Reaction equation

HRID 574651 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][C@@H:5]([OH:29])[C@@H:6]2[N:12]1[C:20]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]=2[C:14]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[C:24]#[N:25])=[N:13]1.C(N(CC)CC)C.[CH2:37]([N:39]=[C:40]=[O:41])[CH3:38]>C(Cl)Cl>[CH2:37]([NH:39][C:40]([N:17]1[CH2:18][CH2:19][C:20]2[N:12]([C@@H:6]3[C:7]4[C:3](=[C:2]([Cl:1])[CH:10]=[C:9]([Cl:11])[CH:8]=4)[CH2:4][C@H:5]3[OH:29])[N:13]=[C:14]([C:21]3[CH:28]=[CH:27][CH:26]=[C:23]([C:24]#[N:25])[CH:22]=3)[C:15]=2[CH2:16]1)=[O:41])[CH3:38]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 89444385HCID 89444385, compound

Product 1

HCID 89444146HCID 89444146, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 17: To a solution of 3-[1-((1R,2R)-4,6-dichloro-2-hydroxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (13e) (0.03 g, 0.071 mmol) in dry CH2Cl2 at 0° C. triethylamine (57 mg, 0.564 mmol) and ethylisocyanate (5.5 mg, 0.077 mmol) was added. The mixture was stirred for 1 h at room temperature and purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 31 mg of 3-(3-cyano-phenyl)-1-((1R,2R)-4,6-dichloro-2-hydroxy-indan-1-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid ethylamide (22a)

Workup

  1. custompurified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4352c274e9d742f385c154986c038df2
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

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