Hydrochloric Acid → N-{3-chloro-4-[(6-methylpyridin-2-yl)methoxy]phenyl}-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine

HRID 222037Notes

Reaction equation

HRID 222037 reaction equation
C(O)(C)C.Cl[C:6]1[C:7]2[C:14]3[CH2:15][CH2:16][C:17]4([CH2:22][C:13]=3[S:12][C:8]=2[N:9]=[CH:10][N:11]=1)[O:21][CH2:20][CH2:19][O:18]4.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[N:34]=1)[NH2:27].Cl>O1CCOCC1>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:6]2[C:7]3[C:14]4[CH2:15][CH2:16][C:17]5([CH2:22][C:13]=4[S:12][C:8]=3[N:9]=[CH:10][N:11]=2)[O:21][CH2:20][CH2:19][O:18]5)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[N:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 179901054-chloro-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolane]HCID 220552383-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

Product 1

HCID 58346456N-{3-chloro-4-[(6-methylpyridin-2-yl)methoxy]phenyl}-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To isopropanol (80 mL) was sequentially added 4-chloro-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2′-[1,3]dioxolane] (5.5 g, 19.4 mmol), 3-chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline (4.61 g, 18.5 mmol), and 4N HCl in dioxane (0.8 mL). The suspension was stirred with heating to 80° C., upon which time the contents turn brown and homogeneous. After 8 h, the heterogeneous mixture was removed from heating, and allowed to cool to rt. The resultant precipitate was collected by filtration as a light-brown solid (5.67 g, 81%), which was used without further purification. 1H-NMR (DMSO-d6) δ 8.35 (s, 1H), 8.16 (s, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.51 (dd, 1H), 7.34 (d, 1H), 7.21 (m, 1H), 7.19 (d, 1H), 5.21 (s, 2H), 3.97 (s, 4H), 3.26 (t, 2H), 3.01 (s, 2H), 2.48 (s, 3H), 1.95 (t, 2H); LCMS RT=2.78 min; [M+H]+=495.2.

Workup

  1. customthe heterogeneous mixture was removed
  2. temperaturefrom heating
  3. temperatureto cool to rt
  4. filtrationThe resultant precipitate was collected by filtration as a light-brown solid (5.67 g, 81%), which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-d0da7a589d434dfa8c1efa52aeeaaf7d
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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