N-(tert-butoxycarbonyl)glycine → HCID 135839329, compound

HRID 724422Notes

Reaction equation

HRID 724422 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH:6]=[CH:7][C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=4)=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([NH:38][CH2:39][C:40](O)=[O:41])(OC(C)(C)C)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.CN(C1C=CN=CC=1)C>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:12]=[C:11]3[C:16]([C:8](/[CH:7]=[CH:6]/[C:5]4[CH:29]=[CH:30][C:2]([NH:1][C:40](=[O:41])[CH2:39][NH2:38])=[CH:3][CH:4]=4)=[N:9][NH:10]3)=[CH:15][CH:14]=2)=[CH:18][C:19]=1[O:27][CH3:28]

Participants

6

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69371043HCID 69371043, compound

Product 1

HCID 135839329HCID 135839329, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-aminostyryl)-6-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazole (90 mg, 0.224 mmol) was dissolved in dichloromethane (2 mL) and was treated with Boc-glycine (196 mg, 1.12 mmol, 5 equiv), DMAP (82 mg, 3 equiv) and HATU (426 mg, 5 equiv). The mixture was allowed to stir for 30 min. The mixture was partitioned between ethyl acetate and water. The organic material was concentrated, taken up in methanol (5 mL) and was treated with potassium carbonate (100 mg). The mixture was heated to 50° C. for 3 d. The resulting mix was again partitioned between ethyl acetate and water. The organic material was concentrated, and purified by silica (109 mg, 66%): Rf sm 0.32, p 0.46 (ethyl acetate-hexane 6:4); 1H NMR (300 MHz, CDCl3) δ 8.18 (bs, 1H), 8.03 (d, 1H, J=8.1 Hz), 7.56 (m, 5H), 7.40 (m, 3H), 7.20 (m, 3H), 5.29 (s, 2H), 5.20 (bs, 1H), 3.98 (s, 3H), 3.96 (d, 2H), 3.54 (s, 3H), 1.48 (s, 9H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. concentrationThe organic material was concentrated
  3. additionwas treated with potassium carbonate (100 mg)
  4. additionThe resulting mix
  5. customwas again partitioned between ethyl acetate and water
  6. concentrationThe organic material was concentrated
  7. custompurified by silica (109 mg, 66%)

Sources & evidence

ORD record
ord-f80c4b7c0b4242b68801ef2886248e80
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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