Dichloromethane → HCID 86689541, compound

HRID 1853861Notes

Reaction equation

HRID 1853861 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:24][CH3:25])=[CH:19][CH:18]=1.B(Br)(Br)Br.C(Cl)[Cl:39]>>[ClH:39].[NH2:26][C@@H:23]([C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[OH:2])=[CH:22][CH:21]=1)[CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86689503HCID 86689503, compound

Product 1

HCID 86689541HCID 86689541, compoundYield 67%

Procedure

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (70 mg, 0.15 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (35 mg, 67%): 1H NMR (500 MHz, CD3OD) δ 7.61 (s, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.45-7.40 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 5.9 Hz, 1H), 2.23-2.01 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.06 min.

Workup

  1. customat 0° C.
  2. customThe reaction was quenched
  3. additionby pouring onto water or ice-water
  4. concentrationthe resulting mixture was concentrated
  5. custompurified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient)
  6. dissolutionThe desired product was dissolved in aqueous HCl
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-c7c8f863d826417586dd35f30cd8cf3d
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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