3-(Trifluoromethoxy)benzylamine → HCID 18922802, compound

HRID 1289917Notes

Reaction equation

HRID 1289917 reaction equation
C(O[C:4]1[C:5](=[O:14])[C:6](=[O:13])[C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])C.C(OC1C(=O)C(=O)C=1N[C@H](C)C(C)(C)C)C.[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37][NH2:38].[K+].[Br-]>>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:38][CH2:37][C:36]1[CH:39]=[CH:40][CH:41]=[C:34]([O:33][C:32]([F:31])([F:42])[F:43])[CH:35]=1)([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 4

HCID 1452643-(Trifluoromethoxy)benzylamineHCID 253877Potassium BromideHCID 19082433HCID 19082433, compoundHCID 54525291HCID 54525291, compound

Product 1

HCID 18922802HCID 18922802, compoundYield 66%

Procedure

The title compound was prepared according to the procedure for example 1-step 2 except that 3-ethoxy-4-(tert-butylamino)-cyclobut-3-ene-1,2-dione was used in place of using (R)-3-ethoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione and 3-trifluoromethoxy-benzylamine was used in place of 4-fluorobenzylamine. Yield: 66%; mp: 210-212° C.; 1H NMR (300 MHz, DMSO-d6): δ 1.36 (m, 9H), 4.76-4.81 (m 2H), 7.32-7.43 (m, 3H), 7.50-7.60 (m, 2H), 7.76-7.84 (brm, 1H); IR (KBr, cm-1): 3295m, 3239m, 3063w, 2973m, 1794m, 1655s, 1569s, 1542s, 1471s, 1446s, 1259-1168brs; MS (ES) m/z (relative intensity): 365 (M+ +Na, 50), 343 (M+ +H, 100); Anal. Calcd. for C16H17F3N2O3 : C, 56.14; H, 5.01; N, 8.18. Found: C, 55.91; H, 4.70; N, 7.99.

Sources & evidence

ORD record
ord-401fa0692abf4f53bfbb930bc98b7088
Source dataset
uspto-grants-1998_05
Patent number
US05750574

Reaction notes

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