HCID 58303866, compound → HCID 58303872, compound

HRID 1404108Notes

Reaction equation

HRID 1404108 reaction equation
[CH2:1]([NH:8]CCC1C2C(=CC=C(F)C=2OC)N(C)C=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([N:26]1[C:34]2[C:29](=[C:30]([O:36][CH3:37])[CH:31]=[CH:32][C:33]=2[F:35])[C:28]([CH2:38][CH2:39]O)=[CH:27]1)[CH3:25]>>[CH2:1]([NH:8][CH2:39][CH2:38][C:28]1[C:29]2[C:34](=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[O:36][CH3:37])[N:26]([CH2:24][CH3:25])[CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 58303866HCID 58303866, compoundHCID 58303927HCID 58303927, compound

Product 1

HCID 58303872HCID 58303872, compoundYield 68%

Procedure

Following the procedure (step 6, scheme 17) used to prepare compound 17-7, compound 20-3 was used as starting material, giving compound 20-4 in 68% yield as a white solid, which was converted to the hydrochloride salt. 1H NMR (DMSO-d6, 300 MHz) δ (ppm) (HCl salt): 9.25 (br, 2H), 7.54-7.57 (m, 2H), 7.42-7.44 (m, 3H), 7.16 (s, 1H), 6.82 (dd, J=12.4, 8.5 Hz, 1H), 6.35 (dd, J=8.5, 2.7 Hz, 1H), 4.21 (q, J=7.1 Hz, 2H), 4.17 (s, 2H), 3.75 (s, 3H), 3.12 (br, 4H), 1.32 (t, J=7.1 Hz, 3H). LRMS: calc 326.2 found 327.2 [MH]+.

Sources & evidence

ORD record
ord-cdf56131eba54fbc973e7a88406eb2fa
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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