Ethanol → HCID 68802545, compound

HRID 505751Notes

Reaction equation

HRID 505751 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:17]3[C:12]([C:13]4[CH:29]=[CH:28][C:27]([C:30]([OH:32])=O)=[CH:26][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(O)C.[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:17]3[C:12]([C:13]4[CH:29]=[CH:28][C:27]([C:30]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:32])=[CH:26][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

8

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24983756HCID 24983756, compound

Product 1

HCID 68802545HCID 68802545, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-(3RS,3aRS)-2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 2 (45 mg, 0.10 mmol), methylsulfonamide (12 mg, 0.12 mmol), triethylamine (0.021 mL, 0.15 mmol), and tetrahydrofuran (1.0 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol) followed by 4-dimethylaminopyridine (15 mg, 0.12 mmol) at room temp. The reaction was stirred at room temp overnight. The reaction was concentrated and purified by reverse-phase HPLC (40 to 95% acetonitrile/water/0.05% trifluoroacetic acid) to give the title compound (yellow solid, 20.6 mg, 0.0394 mmol, 39% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70-0.92 (m, 1H), 1.72-1.89 (m, 1H), 2.84-3.04 (m, 2H), 3.35 (s, 3H), 3.98 (ddd, J=13.67, 10.94, 5.08 Hz, 1H), 5.95 (d, J=11.33 Hz, 1H), 6.65-7.58 (m, 6H), 7.67 (d, J=8.98 Hz, 1H), 7.75-7.89 (m, 2H), 8.16 (d, J=8.20 Hz, 1H), 12.17 (s, 1H). ES-MS m/z 523 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reverse-phase HPLC (40 to 95% acetonitrile/water/0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-24dbf2f72ce148eb84a8a2da9e958b05
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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