Potassium Bromide → HCID 71277786, compound

HRID 62137Notes

Reaction equation

HRID 62137 reaction equation
[C:1]([C:3]1[S:4][C:5]2[C:11]([C:12]#[N:13])=[C:10](/[N:14]=[CH:15]/[N:16](C)C)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[N:19]1([C:24]2[CH:30]=[CH:29][C:27](N)=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[N:19]1([C:24]2[CH:30]=[CH:29][C:27]([NH:13][C:12]3[C:11]4[C:10](=[CH:9][CH:8]=[C:6]5[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]5=4)[N:14]=[CH:15][N:16]=3)=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 8088414-(Pyrrolidin-1-yl)anilineHCID 178484237HCID 178484237, compound

Product 1

HCID 71277786HCID 71277786, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-(pyrrolidin-1-yl)aniline. Flash chromatography eluent (DCM-EtOAc, 8:2). Yield: 48%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3303, 2842, 2233, 1709, 1629, 1613, 1583, 1522, 1466, 1388, 1347, 1275, 1219, 1185, 1166, 1060, 1014, 989, 828, 809; 1H NMR (300 MHz, DMSO-d6) δ 8.54 (d, 1H, J=9.0 Hz), 8.15 (s, 1H), 7.88 (d, 1H, J=9.0 Hz), 7.35 (d, 2H, J=8.1 Hz), 6.73 (d, 2H, J=8.1 Hz), 3.17 (m, 4H), 1.99 (m, 4H); HRMS calcd for C20H17N6S (M+H+): 373.1235, found 373.1218.

Sources & evidence

ORD record
ord-00fd3479b5ca4d61b00ff8360af6f2cc
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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