(S)-(+)-2-(Methoxymethyl)pyrrolidine → HCID 59232221, compound

HRID 1099285Notes

Reaction equation

HRID 1099285 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.[Br:9][C:10]1[CH:11]=[C:12]([CH2:20][CH2:21][CH2:22]N2CCOCC2)[N:13]2[C:18]=1[C:17]([NH2:19])=[N:16][CH:15]=[N:14]2>>[Br:9][C:10]1[CH:11]=[C:12]([CH2:20][CH2:21][CH2:22][N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[CH2:3][O:2][CH3:1])[N:13]2[C:18]=1[C:17]([NH2:19])=[N:16][CH:15]=[N:14]2

Participants

3

Reactant 2

HCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 59232042HCID 59232042, compound

Product 1

HCID 59232221HCID 59232221, compound

Procedure

Intermediate V step 4 (947 mg, 2.8 mmol) was allowed to react with (2S)-2-(methoxymethyl)pyrrolidine (980 mg, 8.5 mmol) using the procedure to make 5-bromo-7-(3-morpholin-4-ylpropyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine. The reaction was partitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with EtOAc (10 mL). The combined organic layer was washed with brine (10 mL) then dried with sodium sulfate. The reaction was concentrated under vacuum to quantitatively yield crude product. 1H-NMR (DMSO-d6) 7.83 (s, 1H), 6.61 (s, 1H), 3.25 (m, 1H), 3.19 (s, 3H), 3.12 to 2.72 (m, 6H), 2.23 (m, 1H), 2.04 (m, 1H), 1.77 (m, 3H), 1.62 (m, 2H), 1.40 (m, 1H); MS [M+H]+=622.2; LCMS RT=2.68.

Workup

  1. customThe reaction was partitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (20 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  3. washThe combined organic layer was washed with brine (10 mL)
  4. dry with materialthen dried with sodium sulfate
  5. concentrationThe reaction was concentrated under vacuum
  6. customto quantitatively yield crude product
  7. customLCMS RT=2.68

Sources & evidence

ORD record
ord-5dcb4efe5977415f9226fa72315b4fcc
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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