Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1) → HCID 59429313, compound

HRID 505755Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C@@H:18]([C:19]3[O:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[C@@H:17]3[C:12]([C:13]4[CH:28]=[CH:27][C:26]([C:29]([OH:31])=O)=[CH:25][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[CH3:33][S:34]([CH2:37][CH2:38][NH2:39])(=[O:36])=[O:35]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C@@H:18]([C:19]3[O:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[C@@H:17]3[C:12]([C:13]4[CH:28]=[CH:27][C:26]([C:29]([NH:39][CH2:38][CH2:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:31])=[CH:25][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

Reactant 2

HCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)

HCID 59429400HCID 59429400, compound

Product 1

HCID 59429313HCID 59429313, compoundYield 70%

Procedure

The title compound was prepared from (3R,3aR)-2-(3-chloro-4-cyanophenyl)-3-(5-methyl-2-furyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 40, and 2-(methylsulfonyl)ethanamine hydrochloride according to Method F (35 mg, 70% yield). 1H NMR (400 MHz, DMSO-d6) water_suppression, δ ppm 1.19-1.21 (m, 1H), 1.91 (d, J=9.88 Hz, 1H), 2.07 (s, 3H), 2.96 (d, J=16.84 Hz, 2H), 3.01 (s, 3H), 3.63-3.66 (m, 2H), 3.86 (br. s., 1H), 5.92 (d, J=16.47 Hz, 1H), 5.95 (br. s., 1H), 6.27 (d, J=2.93 Hz, 1H), 7.06 (br. s., 1H), 7.33 (br. s., 1H), 7.65-7.74 (m, 3H), 8.08 (d, J=8.05 Hz, 1H), 8.77 (t, J=5.49 Hz, 1H); ES-MS m/z 537 (M+H).

Sources & evidence

ORD record: ord-8431937138d14df9963d863576fa2873
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781428B2

Reaction notes

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