Isopropylamine → HCID 18439681, compound

HRID 457577Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([C:15]3[O:19][C:18]([NH:20][C:21]4[CH:26]=[C:25]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=4[O:32][CH3:33])=[N:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH:34]([NH2:37])([CH3:36])[CH3:35]>>[CH2:30]([S:27]([C:25]1[CH:24]=[CH:23][C:22]([O:32][CH3:33])=[C:21]([NH:20][C:18]2[O:19][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:37][CH:34]([CH3:36])[CH3:35])[N:7]=3)=[CH:16][N:17]=2)[CH:26]=1)(=[O:29])=[O:28])[CH3:31]

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 10323158HCID 10323158, compound

Product 1

HCID 18439681HCID 18439681, compoundYield 67%

Conditions

Temperature: 100 °C

Procedure

The title compound of Example 168 (40 mg) was treated with isopropylamine (2 mL) and stirred at 100° C. overnight in a sealed tube. The mixture was evaporated to dryness and purified by thin layer chromatography to afford the title compound (28 mg, 67% yield) as a yellow solid, which was isolated as the HCl salt 1H NMR (400 MHz, d6-DMSO): δ 9.77 (bs, 1H), 8.68 (s, 1H), 8.26 (d, J=6.4, 1H), 7.58 7.45 (m, 5H), 7.23 (d, J=8.4, 1H), 7.14 (m, 1H), 6.61–6.64 (m, 2H), 3.92 (s, 3H), 3.32 (m, 1H), 3.15 (q, J=7.3, 2H), 1.05 (m, 9H). MS (ES+, m/z)=510 (m+H)+.

Workup

customThe mixture was evaporated to dryness
custompurified by thin layer chromatography

Sources & evidence

ORD record: ord-3f2b642f068142619476b39438459f39
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189712B2

Reaction notes

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