Pyrrolidine → HCID 66653277, compound

HRID 1035208Notes

Reaction equation

HRID 1035208 reaction equation
FC1C=C(O)C=CC=1CN1CCN(C)CC1.F[C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][C:35]=1[CH2:36][N:37]1[CH2:42][CH2:41]N(C)[CH2:39][CH2:38]1)[O:21][CH:22]1[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]1.N1CC(OC2C=CC(CN3CCN(C)CC3)=C(F)C=2)C1.N1CCCC1.COC1C=CC(C=O)=C([C:79]([F:82])([F:81])[F:80])C=1>>[NH:24]1[CH2:23][CH:22]([O:21][C:20]2[CH:33]=[CH:34][C:35]([CH2:36][N:37]3[CH2:38][CH2:39][CH2:41][CH2:42]3)=[C:18]([C:79]([F:82])([F:81])[F:80])[CH:19]=2)[CH2:25]1

Participants

6

Reactant 5

HCID 31268PyrrolidineHCID 27782864-Methoxy-2-(trifluoromethyl)benzaldehydeHCID 580431263-Fluoro-4-((4-methylpiperazin-1-yl)methyl)phenolHCID 58043154tert-Butyl 3-(3-fluoro-4-((4-methylpiperazin-1-yl)methyl)phenoxy)azetidine-1-carboxylateHCID 666534801-(4-(Azetidin-3-yloxy)-2-fluorobenzyl)-4-methylpiperazine

Product 1

HCID 66653277HCID 66653277, compoundYield 20%

Procedure

Using similar protocols as described in Examples 29A, 29B, 29C and 29D employing pyrrolidine and 4-methoxy-2-(trifluoromethyl)benzaldehyde as starting materials afforded 0.58 g (20%) of 45A as an oil. 1H NMR (500 MHz, CDCl3): δ 1.78 (s, 4H), 2.53 (d, 4H), 3.71 (s, 2H), 3.80 (m, 2H), 3.93 (m, 2H), 5.01 (m, 1H), 6.87 (dd, 1H), 7.00 (d, 1H), 7.64 (d, 1H), MS (APCI+) m/z 301 [M+H]+.

Sources & evidence

ORD record
ord-dead17049d1a410894c783ab1f9fb40a
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…