Hydrogen Sulfide → HCID 59300533, compound

HRID 603456Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:29][CH2:30][CH3:31])[CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18][CH2:17]3)=[N:7][CH:8]=1)#[N:2].[SH2:32].C(NCC)C>CN(C=O)C>[NH2:2][C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:29][CH2:30][CH3:31])[CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18][CH2:17]3)=[N:7][CH:8]=1)=[S:32]

Participants

Conditions

Temperature: 60 °C

Procedure

Through a solution of ethyl ((1S)-5-{3-[(5-cyano-2-yridinyl)(propyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 265) (0.62 g, 1.47 mmol) in DMF (7 mL) at rt for 20 min was gently passed H2S. Diethylamine (0.23 mL, 2.21 mmol) was added in one portion, and the resultant light green solution was heated at 60° C. for 3 h. Upon completion of the reaction, the dark green solution was purged with a strong flow of argon, and then concentrated under reduced pressure. The product (0.63 g, 95%) was isolated after silica gel column chromatography (1:1 hexanes/EtOAc) as a yellow solid. 1H NMR (400 MHz, CD2Cl2) δ 8.68 (d, 1H), 8.02 (dd, 1H), 7.30 (b, 1H), 7.15-7.02 (m, 2H), 6.79 (d, 1H), 6.71 (dd, 1H), 6.49 (d, 1H), 4.16 (q, 2H), 4.00 (t, 2H), 3.75 (t, 2H), 3.56-3.45 (m, 3H), 2.96-2.78 (m, 2H), 2.75-2.68 (m, 1H), 2.48-2.34 (m, 2H), 2.11 (qt, 2H), 1.82-1.60 (m, 3H), 1.28 (t, 3H), 0.97 (t, 3H).

Workup

customUpon completion of the reaction
customthe dark green solution was purged with a strong flow of argon
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-910cc074263344ad859a1f86b4d57e10
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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